A Synthesis of Exiguaquinol Dessulfate

A concise and stereoselective synthesis of exiguaquinol dessulfate is described. Sequential application of a Diels–Alder cycloaddition, a desymmetrizing aldol addition, and a reductive Heck cyclization established most of the architecture of exiguaquinol, and a carefully choreographed introduction o...

Full description

Saved in:

Bibliographic Details
Published in:	Chemistry : a European journal Vol. 22; no. 50; pp. 17953 - 17957
Main Authors:	Schwarzwalder, Gregg M., Scott, David R., Vanderwal, Christopher D.
Format:	Journal Article
Language:	English
Published:	WEINHEIM Blackwell Publishing Ltd 12.12.2016 Wiley Wiley Subscription Services, Inc
Subjects:	Aldehydes Aldehydes - chemistry antibiotics Architecture Chemistry Chemistry, Multidisciplinary Congeners Culture Cyclization Cycloaddition Reaction epimers Forges Heck cyclization Hydrogen bonding Hydroquinones - chemical synthesis Hydroquinones - chemistry Molecular Structure natural product synthesis Physical Sciences Science & Technology Strategy sulfation Synthesis CORE SELECTIVE ANTIBACTERIAL AGENTS PYLORI GLUTAMATE RACEMASE natural product synthesis MARINE SPONGE 3,6-DIMETHOXYBENZOCYCLOBUTENONE PYRIDODIAZEPINE AMINES GASTRIC-CANCER Heck cyclization epimers sulfation INHIBITORS antibiotics HELICOBACTER-PYLORI ALKALOID JAMTINE
ISSN:	0947-6539, 1521-3765, 1521-3765
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Abstract	A concise and stereoselective synthesis of exiguaquinol dessulfate is described. Sequential application of a Diels–Alder cycloaddition, a desymmetrizing aldol addition, and a reductive Heck cyclization established most of the architecture of exiguaquinol, and a carefully choreographed introduction of the polar substituents afforded the title compound; unfortunately, naphthoquinol sulfation could not be achieved to deliver exiguaquinol. Our hypothesis regarding the configurational preference of the N‐acyl hemiaminal, which was based upon an analysis of internal hydrogen‐bonding interactions with polar functional groups, was proven correct. A late‐stage intermediate did not demonstrate bactericidal activity against H. pylori cultures. A desymmetrization strategy led to the synthesis of a congener of exiguaquinol, an inhibitor of the H. pylori MurI enzyme and a potential antibiotic. The pentacyclic architecture was accessed through convergent Diels–Alder and aldol additions, followed by a reductive Heck cyclization to forge the vicinal quaternary stereogenic centers.
AbstractList	A concise and stereoselective synthesis of exiguaquinol dessulfate is described. Sequential application of a Diels-Alder cycloaddition, a desymmetrizing aldol addition, and a reductive Heck cyclization established most of the architecture of exiguaquinol, and a carefully choreographed introduction of the polar substituents afforded the title compound; unfortunately, naphthoquinol sulfation could not be achieved to deliver exiguaquinol. Our hypothesis regarding the configurational preference of the N-acyl hemiaminal, which was based upon an analysis of internal hydrogen-bonding interactions with polar functional groups, was proven correct. A late-stage intermediate did not demonstrate bactericidal activity against H. pylori cultures.A concise and stereoselective synthesis of exiguaquinol dessulfate is described. Sequential application of a Diels-Alder cycloaddition, a desymmetrizing aldol addition, and a reductive Heck cyclization established most of the architecture of exiguaquinol, and a carefully choreographed introduction of the polar substituents afforded the title compound; unfortunately, naphthoquinol sulfation could not be achieved to deliver exiguaquinol. Our hypothesis regarding the configurational preference of the N-acyl hemiaminal, which was based upon an analysis of internal hydrogen-bonding interactions with polar functional groups, was proven correct. A late-stage intermediate did not demonstrate bactericidal activity against H. pylori cultures. A concise and stereoselective synthesis of exiguaquinol dessulfate is described. Sequential application of a Diels-Alder cycloaddition, a desymmetrizing aldol addition, and a reductive Heck cyclization established most of the architecture of exiguaquinol, and a carefully choreographed introduction of the polar substituents afforded the title compound; unfortunately, naphthoquinol sulfation could not be achieved to deliver exiguaquinol. Our hypothesis regarding the configurational preference of the N-acyl hemiaminal, which was based upon an analysis of internal hydrogen-bonding interactions with polar functional groups, was proven correct. A late-stage intermediate did not demonstrate bactericidal activity against H. pylori cultures. A concise and stereoselective synthesis of exiguaquinol dessulfate is described. Sequential application of a Diels–Alder cycloaddition, a desymmetrizing aldol addition, and a reductive Heck cyclization established most of the architecture of exiguaquinol, and a carefully choreographed introduction of the polar substituents afforded the title compound; unfortunately, naphthoquinol sulfation could not be achieved to deliver exiguaquinol. Our hypothesis regarding the configurational preference of the N-acyl hemiaminal, which was based upon an analysis of internal hydrogen-bonding interactions with polar functional groups, was proven correct. Unfortunately, the title compound did not demonstrate any bactericidal activity against H. pylori cultures. A desymmetrization strategy led to the synthesis of a congener of exiguaquinol, an inhibitor of the H. pylori MurI enzyme and a potential antibiotic. The pentacyclic architecture was accessed via convergent Diels–Alder and aldol additions, followed by a reductive Heck cyclization to forge the vicinal quaternary stereogenic centers. A concise and stereoselective synthesis of exiguaquinol dessulfate is described. Sequential application of a Diels-Alder cycloaddition, a desymmetrizing aldol addition, and a reductive Heck cyclization established most of the architecture of exiguaquinol, and a carefully choreographed introduction of the polar substituents afforded the title compound; unfortunately, naphthoquinol sulfation could not be achieved to deliver exiguaquinol. Our hypothesis regarding the configurational preference of the N-acyl hemiaminal, which was based upon an analysis of internal hydrogen-bonding interactions with polar functional groups, was proven correct. A late-stage intermediate did not demonstrate bactericidal activity against H. pylori cultures. A desymmetrization strategy led to the synthesis of a congener of exiguaquinol, an inhibitor of the H. pylori MurI enzyme and a potential antibiotic. The pentacyclic architecture was accessed through convergent Diels-Alder and aldol additions, followed by a reductive Heck cyclization to forge the vicinal quaternary stereogenic centers. A concise and stereoselective synthesis of exiguaquinol dessulfate is described. Sequential application of a Diels–Alder cycloaddition, a desymmetrizing aldol addition, and a reductive Heck cyclization established most of the architecture of exiguaquinol, and a carefully choreographed introduction of the polar substituents afforded the title compound; unfortunately, naphthoquinol sulfation could not be achieved to deliver exiguaquinol. Our hypothesis regarding the configurational preference of the N‐acyl hemiaminal, which was based upon an analysis of internal hydrogen‐bonding interactions with polar functional groups, was proven correct. A late‐stage intermediate did not demonstrate bactericidal activity against H. pylori cultures. A desymmetrization strategy led to the synthesis of a congener of exiguaquinol, an inhibitor of the H. pylori MurI enzyme and a potential antibiotic. The pentacyclic architecture was accessed through convergent Diels–Alder and aldol additions, followed by a reductive Heck cyclization to forge the vicinal quaternary stereogenic centers.
Author	Scott, David R. Vanderwal, Christopher D. Schwarzwalder, Gregg M.
AuthorAffiliation	a Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, CA, 92697-2025, USA b Department of Physiology, 11310 Wilshire Blvd, Bldg. 113, Rm. 324, UC Los Angeles/VA Greater Los Angeles Healthcare System, Los Angeles, CA, 90073, USA
AuthorAffiliation_xml	– name: b Department of Physiology, 11310 Wilshire Blvd, Bldg. 113, Rm. 324, UC Los Angeles/VA Greater Los Angeles Healthcare System, Los Angeles, CA, 90073, USA – name: a Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, CA, 92697-2025, USA
Author_xml	– sequence: 1 givenname: Gregg M. surname: Schwarzwalder fullname: Schwarzwalder, Gregg M. organization: Department of Chemistry, University of California, 1102 Natural Sciences II, CA, 92697-2025, Irvine, USA – sequence: 2 givenname: David R. surname: Scott fullname: Scott, David R. organization: Department of Physiology, UC Los Angeles/VA Greater Los Angeles Healthcare System, 11310 Wilshire Blvd, Bldg. 113, Rm. 324, CA, 90073, Los Angeles, USA – sequence: 3 givenname: Christopher D. surname: Vanderwal fullname: Vanderwal, Christopher D. email: cdv@uci.edu organization: Department of Chemistry, University of California, 1102 Natural Sciences II, CA, 92697-2025, Irvine, USA
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/27673578$$D View this record in MEDLINE/PubMed
BookMark	eNqNks1vEzEQxS1URNPAlSOKhISQ0AZ_re29IFXbkCIKHMrH0fI648ZlY7frXWj-exwljUolRE-2NL83fn4zR-ggxAAIPSd4SjCmb-0SVlOKicC8xOIRGpGSkoJJUR6gEa64LETJqkN0lNIlxrgSjD1Bh1QKyUqpRujV8eR8HfolJJ8m0U1mN_5iMNeDD7GdnEBKQ-tMD0_RY2faBM925xh9ez_7Wp8WZ1_mH-rjs8IKTkVBOXOYEKDOkYVxhIKQykpSslKoBTOsaWwpGgEMgFtFmeGNkxYWrrKKNI6N0btt36uhWcHCQug70-qrzq9Mt9bReP13Jfilvoi_tMBUYUxyg9e7Bl28HiD1euWThbY1AeKQNFGCZy-M0QegG9dC5U-N0ct76GUcupCTyBRXCleEi0y9uGt-7_o27Qy82QK_oYkuWQ_Bwh7L42EVzoMU-UY2_tTD6dr3pvcx1HEIfZbyrdR2MaUOnLa7eg7Nt5pgvdkevdkevd-eLJvek92-9k9BtbPoW1j_h9b16ezTXW2x1frUw81ea7qfOsclS_3j81yTk0p-P_841zX7A-zI4xE
CODEN	CEUJED
CitedBy_id	crossref_primary_10_1055_a_2627_8429 crossref_primary_10_1246_cl_200841 crossref_primary_10_1039_D0QO01346C crossref_primary_10_1002_ejoc_201601418 crossref_primary_10_1039_D5OB00692A crossref_primary_10_1002_slct_201804029
Cites_doi	10.1021/ja505131v 10.1016/S0040-4020(01)81452-6 10.1021/jo0266339 10.1002/anie.201109221 10.1136/gutjnl-2012-302084 10.1016/j.bmcl.2012.07.004 10.1111/j.1751-7915.2008.00031.x 10.1021/ol027447s 10.1016/S0040-4039(00)81783-9 10.1016/S0040-4020(02)01089-X 10.1128/AAC.04410-14 10.1021/ja984113i 10.1021/ol800898z 10.1111/j.1469-0691.2009.03031.x 10.1021/jo951978v 10.1001/jama.291.2.187 10.1038/nature05689 10.1039/P19940002137 10.1021/ja0002058 10.1016/S0040-4020(01)87872-8 10.1002/anie.201206558 10.1248/cpb.33.1305 10.1021/ja00233a026 10.1021/ol036157o 10.1016/j.tetlet.2004.02.010 10.1016/j.bmcl.2008.11.113 10.1002/ange.201109221 10.1016/j.bmcl.2008.06.092 10.1016/S0957-4166(00)82150-3 10.1002/cctc.201300853 10.1038/nrc2857 10.1021/jo00114a054 10.1021/ol402905n 10.1128/AAC.00226-09 10.1016/j.tet.2003.08.046 10.1021/ja5078188 10.1021/ol0526468 10.1021/ja00357a049 10.1016/S0022-328X(00)90287-0 10.1002/ange.201206558 10.1021/ja01043a041
ContentType	Journal Article
Copyright	2016 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Copyright_xml	– notice: 2016 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim – notice: 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. – notice: 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
DBID	BSCLL AAYXX CITATION 17B 1KM BLEPL DTL EGQ GYFQL CGR CUY CVF ECM EIF NPM 7SR 8BQ 8FD JG9 K9. 7X8 5PM
DOI	10.1002/chem.201604506
DatabaseName	Istex CrossRef Web of Knowledge Index Chemicus Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) Web of Science - Science Citation Index Expanded - 2016 Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed Engineered Materials Abstracts METADEX Technology Research Database Materials Research Database ProQuest Health & Medical Complete (Alumni) MEDLINE - Academic PubMed Central (Full Participant titles)
DatabaseTitle	CrossRef Web of Science MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) Materials Research Database ProQuest Health & Medical Complete (Alumni) Engineered Materials Abstracts Technology Research Database METADEX MEDLINE - Academic
DatabaseTitleList	MEDLINE - Academic Materials Research Database MEDLINE Materials Research Database CrossRef Web of Science
Database_xml	– sequence: 1 dbid: NPM name: PubMed url: http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: 1KM name: Index Chemicus url: https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database – sequence: 3 dbid: 7X8 name: MEDLINE - Academic url: https://search.proquest.com/medline sourceTypes: Aggregation Database
DeliveryMethod	fulltext_linktorsrc
Discipline	Chemistry Architecture
EISSN	1521-3765
EndPage	17957
ExternalDocumentID	PMC6028001 4278267451 27673578 000390604600012 10_1002_chem_201604506 CHEM201604506 ark_67375_WNG_1D97VSKG_C
Genre	shortCommunication Journal Article
GrantInformation_xml	– fundername: NIH; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA grantid: CA180568 – fundername: NATIONAL CANCER INSTITUTE; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Cancer Institute (NCI) grantid: F31CA180568
GroupedDBID	--- -DZ -~X .3N .GA 05W 0R~ 10A 1L6 1OB 1OC 1ZS 29B 33P 3SF 3WU 4.4 4ZD 50Y 50Z 51W 51X 52M 52N 52O 52P 52S 52T 52U 52W 52X 53G 5GY 5VS 66C 6J9 702 77Q 7PT 8-0 8-1 8-3 8-4 8-5 8UM 930 A03 AAESR AAEVG AAHQN AAMNL AANLZ AAONW AASGY AAXRX AAYCA AAZKR ABCQN ABCUV ABDBF ABIJN ABJNI ABLJU ABPVW ACAHQ ACCZN ACGFS ACIWK ACNCT ACPOU ACUHS ACXBN ACXQS ADBBV ADEOM ADIZJ ADKYN ADMGS ADOZA ADXAS ADZMN AEGXH AEIGN AEIMD AEUYR AEYWJ AFBPY AFFPM AFGKR AFRAH AFWVQ AFZJQ AGHNM AGYGG AHBTC AHMBA AITYG AIURR AJXKR ALAGY ALMA_UNASSIGNED_HOLDINGS ALVPJ AMBMR AMYDB ATUGU AUFTA AZBYB AZVAB BAFTC BDRZF BFHJK BHBCM BMNLL BMXJE BNHUX BROTX BRXPI BSCLL BY8 CS3 D-E D-F DCZOG DPXWK DR2 DRFUL DRSTM EBD EBS EJD F00 F01 F04 F5P G-S G.N GNP GODZA H.T H.X HBH HGLYW HHY HHZ HZ~ IX1 J0M JPC KQQ LATKE LAW LC2 LC3 LEEKS LH4 LITHE LOXES LP6 LP7 LUTES LW6 LYRES MEWTI MK4 MRFUL MRSTM MSFUL MSSTM MXFUL MXSTM N04 N05 N9A NF~ NNB O66 O9- OIG P2W P2X P4D PQQKQ Q.N Q11 QB0 QRW R.K RNS ROL RX1 RYL SUPJJ TN5 TWZ UB1 UPT V2E V8K W8V W99 WBFHL WBKPD WH7 WIB WIH WIK WJL WOHZO WQJ WXSBR WYISQ XG1 XPP XV2 YZZ ZZTAW ~IA ~WT AAHHS ACCFJ ADZOD AEEZP AEQDE AEUQT AFPWT AIWBW AJBDE RGC RWI WRC AAYXX CITATION O8X 17B 1KM BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED GROUPED_WOS_WEB_OF_SCIENCE CGR CUY CVF ECM EIF NPM 7SR 8BQ 8FD JG9 K9. 7X8 5PM
ID	FETCH-LOGICAL-c6426-243f011e2ff1daf12e678c7153568d3a3bbc56b6e3ee4c823a4bf7cedf9c81bf3
IEDL.DBID	DRFUL
ISICitedReferencesCount	8
ISICitedReferencesURI	https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000390604600012
ISSN	0947-6539 1521-3765
IngestDate	Tue Sep 30 16:49:16 EDT 2025 Fri Jul 11 09:53:36 EDT 2025 Fri Jul 11 10:07:45 EDT 2025 Tue Oct 07 06:48:23 EDT 2025 Mon Jul 21 05:45:10 EDT 2025 Wed Jul 09 17:16:03 EDT 2025 Fri Dec 05 22:47:17 EST 2025 Tue Nov 18 22:29:32 EST 2025 Sat Nov 29 07:19:20 EST 2025 Wed Jan 22 16:40:08 EST 2025 Sun Sep 21 06:18:18 EDT 2025
IsDoiOpenAccess	false
IsOpenAccess	true
IsPeerReviewed	true
IsScholarly	true
Issue	50
Keywords	CORE SELECTIVE ANTIBACTERIAL AGENTS PYLORI GLUTAMATE RACEMASE natural product synthesis MARINE SPONGE 3,6-DIMETHOXYBENZOCYCLOBUTENONE PYRIDODIAZEPINE AMINES GASTRIC-CANCER Heck cyclization epimers sulfation INHIBITORS antibiotics HELICOBACTER-PYLORI ALKALOID JAMTINE
Language	English
License	http://onlinelibrary.wiley.com/termsAndConditions#vor 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
LinkModel	DirectLink
LogoURL	https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId	FETCHMERGED-LOGICAL-c6426-243f011e2ff1daf12e678c7153568d3a3bbc56b6e3ee4c823a4bf7cedf9c81bf3
Notes	istex:46151A4580FE3EE8F2EF1C8E75ACC6A29BCEDF33 ArticleID:CHEM201604506 ark:/67375/WNG-1D97VSKG-C NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
ORCID	0000-0001-7218-4521
OpenAccessLink	https://www.ncbi.nlm.nih.gov/pmc/articles/6028001
PMID	27673578
PQID	1848809146
PQPubID	986340
PageCount	5
ParticipantIDs	pubmed_primary_27673578 pubmedcentral_primary_oai_pubmedcentral_nih_gov_6028001 webofscience_primary_000390604600012 crossref_primary_10_1002_chem_201604506 webofscience_primary_000390604600012CitationCount wiley_primary_10_1002_chem_201604506_CHEM201604506 crossref_citationtrail_10_1002_chem_201604506 istex_primary_ark_67375_WNG_1D97VSKG_C proquest_miscellaneous_1835686824 proquest_miscellaneous_1864568332 proquest_journals_1848809146
PublicationCentury	2000
PublicationDate	December 12, 2016
PublicationDateYYYYMMDD	2016-12-12
PublicationDate_xml	– month: 12 year: 2016 text: December 12, 2016 day: 12
PublicationDecade	2010
PublicationPlace	WEINHEIM
PublicationPlace_xml	– name: WEINHEIM – name: Germany – name: Weinheim
PublicationSubtitle	A European Journal
PublicationTitle	Chemistry : a European journal
PublicationTitleAbbrev	CHEM-EUR J
PublicationTitleAlternate	Chem. Eur. J
PublicationYear	2016
Publisher	Blackwell Publishing Ltd Wiley Wiley Subscription Services, Inc
Publisher_xml	– name: Blackwell Publishing Ltd – name: Wiley – name: Wiley Subscription Services, Inc
References	M. Azadi-Ardakani, T. W. Wallace, Tetrahedron 1988, 44, 5939-5952 A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020-4028. N. S. Simpkins, C. D. Gill, Org. Lett. 2003, 5, 535-537 D. Bailey, V. E. Williams, Tetrahedron Lett. 2004, 45, 2511-2513. Y. Lu, D. M. Lemal, J. P. Jasinski, J. Am. Chem. Soc. 2000, 122, 2440-2445. G. M. Schwarzwalder, S. E. Steinhardt, H. V. Pham, K. N. Houk, C. D. Vanderwal, Org. Lett. 2013, 15, 6014-6017. B. Geng, G. Basarab, J. Comita-Previor, M. Gowravaram, P. Hill, A. Kiely, J. Loch, L. MacPherson, M. Morningstar, G. Mullen, E. Osimboni, A. Satz, C. Eyermann, T. Lundqvist, Bioorg. Med. Chem. Lett. 2009, 19, 930-936. B. C. Wong, S. K. Lam, W. M. Wong, J. S. Chen, T. T. Zheng, R. E. Feng, K. C. Lai, W. H. C. Hu, S. T. Yuen, S. Y. Leung, D. Y. T. Fong, J. Ho, C. K. Ching, J. S. Chen, JAMA J. Am. Med. Assoc. 2004, 291, 187-194. D. B. Polk, R. M. Peek, Nat. Rev. Cancer 2010, 10, 403-414 M. W. Hooper, M. Utsunomiya, J. F. Hartwig, J. Org. Chem. 2003, 68, 2861-2873. V. Herrera, J. Parsonnet, Clin. Microbiol. Infect. 2009, 15, 971-976 M. Kobayashi, N. Shimizu, Y. Kyogoku, I. Kitagawa, Chem. Pharm. Bull. 1985, 33, 1305-1308. I. Ayuso-Fernández, M. A. Galmés, A. Bastida, E. García-Junceda, ChemCatChem 2014, 6, 1059-1065. N. G. Andersen, S. P. Maddaford, B. A. Keay, J. Org. Chem. 1996, 61, 2885-2887. Z. Chen, P. Muller, T. M. Swager, Org. Lett. 2006, 8, 273-276. C. P. Hoiberg, R. O. Mumma, J. Am. Chem. Soc. 1969, 91, 4273-4278. N. Harada, T. Sugioka, Y. Ando, H. Uda, T. Kuriki, J. Am. Chem. Soc. 1988, 110, 8483-8487. Angew. Chem. 2012, 124, 12234-12237. C. W. Plummer, C. S. Wei, C. E. Yozwiak, A. Soheili, S. O. Smithback, J. L. Leighton, J. Am. Chem. Soc. 2014, 136, 9878-9881. K. Chiyoda, J. Shimokawa, T. Fukuyama, Angew. Chem. Int. Ed. 2012, 51, 2505-2508 M. Azadi-Ardakani, R. Hayes, T. W. Wallace, Tetrahedron 1990, 46, 6851-6858. N. Iranpoor, H. Firouzabadi, G. Aghapour, A. R. Vaezzadeh, Tetrahedron 2002, 58, 8689-8693. Y. Liu, I.-F. F. Lien, S. Ruttgaizer, P. Dove, S. D. Taylor, Org. Lett. 2004, 6, 209-212. S. L. Fisher, Microbial Biotechnology 2008, 1, 345-360 B. L. M. de Jonge, A. Kutschke, M. Uria-Nickelsen, H. D. Kamp, S. D. Mills, Antimicrob. Agents Chemother. 2009, 53, 3331-3336. P. J. Cox, N. S. Simpkins, Tetrahedron: Asymmetry 1991, 2, 1-26 M. R. Prestly, N. S. Simpkins, Angew. Chem. Int. Ed. 2012, 51, 12068-12071 P. Malfertheiner, F. Megraud, C. A. O'Morain, J. Atherton, A. T. R. Axon, F. Bazzoli, G. F. Gensini, J. P. Gisbert, D. Y. Graham, T. Rokkas, E. M. El-Omar, E. J. Kuipers, Gut 2012, 61, 646-664. T. Lundqvist, S. L. Fisher, G. Kern, R. H. A. Folmer, Y. Xue, D. T. Newton, T. A. Keating, R. A. Alm, B. L. M. de Jonge, Nature 2007, 447, 817-822. M. Azadi-Ardakani, T. W. Wallace, Tetrahedron Lett. 1983, 24, 1829-1832 Angew. Chem. 2012, 124, 2555-2558. C. D. Gill, D. A. Greenhalgh, N. S. Simpkins, Tetrahedron 2003, 59, 9213-9230 G. S. Basarab, P. J. Hill, A. Rastagar, P. J. H. Webborn, Bioorg. Med. Chem. Lett. 2008, 18, 4716-4722 G. S. Basarab, P. Hill, C. J. Eyermann, M. Gowravaram, H. Käck, E. Osimoni, Bioorg. Med. Chem. Lett. 2012, 22, 5600-5607 L. S. Chen, G. J. Chen, C. Tamborski, J. Organomet. Chem. 1980, 193, 283-292. P. de Almeida Leone, A. R. Carroll, L. Towerzey, G. King, B. M. McArdle, G. Kern, S. Fisher, J. N. A. Hooper, R. J. Quinn, Org. Lett. 2008, 10, 2585-2588. J. Ezquerra, C. Pedregal, B. Yruretagoyena, A. Rubio, M. C. Carreno, A. Escribano, J. L. García Ruano, J. Org. Chem. 1995, 60, 2925-2930. B. S. Axelsson, H. G. Floss, S. Lee, A. Saeed, P. A. Spencer, D. W. Young, J. Chem. Soc. Perkin Trans. 1 1994, 2137-2142. B. L. M. de Jonge, A. Kutschke, J. V. Newman, M. T. Rooney, W. Yang, C. Cederberg, Antimicrob. Agents Chemother. 2015, 59, 2337-2342. D. M. Roll, P. J. Scheuer, G. K. Matsumoto, J. Clardy, J. Am. Chem. Soc. 1983, 105, 6177-6178. M. B. Kraft, Y. B. Poudel, N. Kedei, N. E. Lewin, M. L. Peach, P. M. Blumberg, G. E. Keck, J. Am. Chem. Soc. 2014, 136, 13202-13208. 2012; 61 2010; 10 2015; 59 2002; 58 1991; 2 2007; 447 1969; 91 2008; 18 2004; 45 2006; 8 2004; 6 2003; 59 2008; 10 1994 1980; 193 2008; 1 2014; 136 1983; 105 2013; 15 1995; 60 1990; 46 2009; 53 2004; 291 2012 2012; 51 124 1996; 61 2003; 68 1988; 44 2003; 5 1988; 110 2000; 122 1985; 33 2009; 19 2012; 22 2014; 6 1983; 24 2009; 15 e_1_2_2_3_2 e_1_2_2_25_1 e_1_2_2_4_2 e_1_2_2_5_1 e_1_2_2_24_1 e_1_2_2_6_1 e_1_2_2_23_1 e_1_2_2_21_2 e_1_2_2_22_1 e_1_2_2_20_2 e_1_2_2_1_1 e_1_2_2_2_2 e_1_2_2_40_1 e_1_2_2_41_2 e_1_2_2_42_2 e_1_2_2_7_2 e_1_2_2_8_2 e_1_2_2_9_1 e_1_2_2_29_1 e_1_2_2_43_2 e_1_2_2_28_1 e_1_2_2_44_2 e_1_2_2_27_1 e_1_2_2_44_3 e_1_2_2_26_1 e_1_2_2_13_2 e_1_2_2_37_1 e_1_2_2_12_2 e_1_2_2_38_1 e_1_2_2_39_1 e_1_2_2_11_1 e_1_2_2_10_1 e_1_2_2_30_1 e_1_2_2_19_2 e_1_2_2_31_1 e_1_2_2_32_1 e_1_2_2_18_1 e_1_2_2_33_1 e_1_2_2_17_1 e_1_2_2_33_2 e_1_2_2_34_1 e_1_2_2_16_1 e_1_2_2_35_1 e_1_2_2_14_2 e_1_2_2_15_1 e_1_2_2_36_1 AZADIARDAKANI, M (WOS:A1983QM55700022) 1983; 24 de Jonge, BLM (WOS:000354993700060) 2015; 59 AXELSSON, BS (WOS:A1994PC00500019) 1994 AZADIARDAKANI, M (WOS:A1988Q441100028) 1988; 44 Andersen, NG (WOS:A1996UG48300053) 1996; 61 Leone, PD (WOS:000256762100065) 2008; 10 Basarab, GS (WOS:000258769200061) 2008; 18 Herrera, V (WOS:000271055600003) 2009; 15 Fisher, SL (WOS:000207904700004) 2008; 1 Littke, AF (WOS:000086950500005) 2000; 122 HOIBERG, CP (WOS:A1969D665400041) 1969; 91 KOBAYASHI, M (WOS:A1985AFD6700059) 1985; 33 Geng, B (WOS:000262707000083) 2009; 19 Liu, Y (WOS:000188297300017) 2004; 6 COX, PJ (WOS:A1991EX89500001) 1991; 2 Polk, DB (WOS:000278024500011) 2010; 10 Simpkins, NS (WOS:000181077200039) 2003; 5 Malfertheiner, P (WOS:000302776700004) 2012; 61 Ayuso-Fernandez, I (WOS:000334180500025) 2014; 6 AZADIARDAKANI, M (WOS:A1990EA74800024) 1990; 46 Prestly, M. R. (000390604600012.36) 2012; 124 Chen, ZH (WOS:000234657900025) 2006; 8 Schwarzwalder, GM (WOS:000328231500028) 2013; 15 Prestly, MR (WOS:000311705000028) 2012; 51 Chiyoda, K (WOS:000300934700044) 2012; 51 de Jonge, BLM (WOS:000268098300022) 2009; 53 HARADA, N (WOS:A1988R339800026) 1988; 110 Plummer, CW (WOS:000339228200021) 2014; 136 Bailey, D (WOS:000220150900006) 2004; 45 Hooper, MW (WOS:000181953700043) 2003; 68 ROLL, DM (WOS:A1983RH32900049) 1983; 105 EZQUERRA, J (WOS:A1995QX16500054) 1995; 60 Lundqvist, T (WOS:000247207500035) 2007; 447 Wong, BCY (WOS:000188040900026) 2004; 291 Kraft, MB (WOS:000342328200033) 2014; 136 Chiyoda, K. (000390604600012.13) 2012; 124 Basarab, GS (WOS:000308046400048) 2012; 22 Gill, CD (WOS:000186311700018) 2003; 59 CHEN, LS (WOS:A1980KB25700001) 1980; 193 Lu, YC (WOS:000086057200005) 2000; 122 Iranpoor, N (WOS:000178684200005) 2002; 58
References_xml	– reference: B. C. Wong, S. K. Lam, W. M. Wong, J. S. Chen, T. T. Zheng, R. E. Feng, K. C. Lai, W. H. C. Hu, S. T. Yuen, S. Y. Leung, D. Y. T. Fong, J. Ho, C. K. Ching, J. S. Chen, JAMA J. Am. Med. Assoc. 2004, 291, 187-194. – reference: S. L. Fisher, Microbial Biotechnology 2008, 1, 345-360; – reference: C. W. Plummer, C. S. Wei, C. E. Yozwiak, A. Soheili, S. O. Smithback, J. L. Leighton, J. Am. Chem. Soc. 2014, 136, 9878-9881. – reference: M. B. Kraft, Y. B. Poudel, N. Kedei, N. E. Lewin, M. L. Peach, P. M. Blumberg, G. E. Keck, J. Am. Chem. Soc. 2014, 136, 13202-13208. – reference: D. B. Polk, R. M. Peek, Nat. Rev. Cancer 2010, 10, 403-414; – reference: G. S. Basarab, P. J. Hill, A. Rastagar, P. J. H. Webborn, Bioorg. Med. Chem. Lett. 2008, 18, 4716-4722; – reference: Z. Chen, P. Muller, T. M. Swager, Org. Lett. 2006, 8, 273-276. – reference: N. S. Simpkins, C. D. Gill, Org. Lett. 2003, 5, 535-537; – reference: P. Malfertheiner, F. Megraud, C. A. O'Morain, J. Atherton, A. T. R. Axon, F. Bazzoli, G. F. Gensini, J. P. Gisbert, D. Y. Graham, T. Rokkas, E. M. El-Omar, E. J. Kuipers, Gut 2012, 61, 646-664. – reference: B. L. M. de Jonge, A. Kutschke, J. V. Newman, M. T. Rooney, W. Yang, C. Cederberg, Antimicrob. Agents Chemother. 2015, 59, 2337-2342. – reference: C. P. Hoiberg, R. O. Mumma, J. Am. Chem. Soc. 1969, 91, 4273-4278. – reference: P. J. Cox, N. S. Simpkins, Tetrahedron: Asymmetry 1991, 2, 1-26; – reference: Y. Lu, D. M. Lemal, J. P. Jasinski, J. Am. Chem. Soc. 2000, 122, 2440-2445. – reference: N. G. Andersen, S. P. Maddaford, B. A. Keay, J. Org. Chem. 1996, 61, 2885-2887. – reference: M. Kobayashi, N. Shimizu, Y. Kyogoku, I. Kitagawa, Chem. Pharm. Bull. 1985, 33, 1305-1308. – reference: G. S. Basarab, P. Hill, C. J. Eyermann, M. Gowravaram, H. Käck, E. Osimoni, Bioorg. Med. Chem. Lett. 2012, 22, 5600-5607; – reference: M. Azadi-Ardakani, T. W. Wallace, Tetrahedron 1988, 44, 5939-5952; – reference: Y. Liu, I.-F. F. Lien, S. Ruttgaizer, P. Dove, S. D. Taylor, Org. Lett. 2004, 6, 209-212. – reference: V. Herrera, J. Parsonnet, Clin. Microbiol. Infect. 2009, 15, 971-976; – reference: N. Iranpoor, H. Firouzabadi, G. Aghapour, A. R. Vaezzadeh, Tetrahedron 2002, 58, 8689-8693. – reference: G. M. Schwarzwalder, S. E. Steinhardt, H. V. Pham, K. N. Houk, C. D. Vanderwal, Org. Lett. 2013, 15, 6014-6017. – reference: P. de Almeida Leone, A. R. Carroll, L. Towerzey, G. King, B. M. McArdle, G. Kern, S. Fisher, J. N. A. Hooper, R. J. Quinn, Org. Lett. 2008, 10, 2585-2588. – reference: Angew. Chem. 2012, 124, 2555-2558. – reference: K. Chiyoda, J. Shimokawa, T. Fukuyama, Angew. Chem. Int. Ed. 2012, 51, 2505-2508; – reference: C. D. Gill, D. A. Greenhalgh, N. S. Simpkins, Tetrahedron 2003, 59, 9213-9230; – reference: Angew. Chem. 2012, 124, 12234-12237. – reference: M. W. Hooper, M. Utsunomiya, J. F. Hartwig, J. Org. Chem. 2003, 68, 2861-2873. – reference: N. Harada, T. Sugioka, Y. Ando, H. Uda, T. Kuriki, J. Am. Chem. Soc. 1988, 110, 8483-8487. – reference: L. S. Chen, G. J. Chen, C. Tamborski, J. Organomet. Chem. 1980, 193, 283-292. – reference: T. Lundqvist, S. L. Fisher, G. Kern, R. H. A. Folmer, Y. Xue, D. T. Newton, T. A. Keating, R. A. Alm, B. L. M. de Jonge, Nature 2007, 447, 817-822. – reference: M. Azadi-Ardakani, R. Hayes, T. W. Wallace, Tetrahedron 1990, 46, 6851-6858. – reference: I. Ayuso-Fernández, M. A. Galmés, A. Bastida, E. García-Junceda, ChemCatChem 2014, 6, 1059-1065. – reference: M. R. Prestly, N. S. Simpkins, Angew. Chem. Int. Ed. 2012, 51, 12068-12071; – reference: D. Bailey, V. E. Williams, Tetrahedron Lett. 2004, 45, 2511-2513. – reference: M. Azadi-Ardakani, T. W. Wallace, Tetrahedron Lett. 1983, 24, 1829-1832; – reference: J. Ezquerra, C. Pedregal, B. Yruretagoyena, A. Rubio, M. C. Carreno, A. Escribano, J. L. García Ruano, J. Org. Chem. 1995, 60, 2925-2930. – reference: B. S. Axelsson, H. G. Floss, S. Lee, A. Saeed, P. A. Spencer, D. W. Young, J. Chem. Soc. Perkin Trans. 1 1994, 2137-2142. – reference: B. L. M. de Jonge, A. Kutschke, M. Uria-Nickelsen, H. D. Kamp, S. D. Mills, Antimicrob. Agents Chemother. 2009, 53, 3331-3336. – reference: B. Geng, G. Basarab, J. Comita-Previor, M. Gowravaram, P. Hill, A. Kiely, J. Loch, L. MacPherson, M. Morningstar, G. Mullen, E. Osimboni, A. Satz, C. Eyermann, T. Lundqvist, Bioorg. Med. Chem. Lett. 2009, 19, 930-936. – reference: A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020-4028. – reference: D. M. Roll, P. J. Scheuer, G. K. Matsumoto, J. Clardy, J. Am. Chem. Soc. 1983, 105, 6177-6178. – volume: 5 start-page: 535 year: 2003 end-page: 537 publication-title: Org. Lett. – start-page: 2137 year: 1994 end-page: 2142 publication-title: J. Chem. Soc. Perkin Trans. 1 – volume: 33 start-page: 1305 year: 1985 end-page: 1308 publication-title: Chem. Pharm. Bull. – volume: 44 start-page: 5939 year: 1988 end-page: 5952 publication-title: Tetrahedron – volume: 58 start-page: 8689 year: 2002 end-page: 8693 publication-title: Tetrahedron – volume: 15 start-page: 971 year: 2009 end-page: 976 publication-title: Clin. Microbiol. Infect. – volume: 45 start-page: 2511 year: 2004 end-page: 2513 publication-title: Tetrahedron Lett. – volume: 6 start-page: 1059 year: 2014 end-page: 1065 publication-title: ChemCatChem – volume: 110 start-page: 8483 year: 1988 end-page: 8487 publication-title: J. Am. Chem. Soc. – volume: 10 start-page: 403 year: 2010 end-page: 414 publication-title: Nat. Rev. Cancer – volume: 24 start-page: 1829 year: 1983 end-page: 1832 publication-title: Tetrahedron Lett. – volume: 59 start-page: 9213 year: 2003 end-page: 9230 publication-title: Tetrahedron – volume: 8 start-page: 273 year: 2006 end-page: 276 publication-title: Org. Lett. – volume: 51 124 start-page: 12068 12234 year: 2012 2012 end-page: 12071 12237 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 1 start-page: 345 year: 2008 end-page: 360 publication-title: Microbial Biotechnology – volume: 122 start-page: 4020 year: 2000 end-page: 4028 publication-title: J. Am. Chem. Soc. – volume: 91 start-page: 4273 year: 1969 end-page: 4278 publication-title: J. Am. Chem. Soc. – volume: 51 124 start-page: 2505 2555 year: 2012 2012 end-page: 2508 2558 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 46 start-page: 6851 year: 1990 end-page: 6858 publication-title: Tetrahedron – volume: 10 start-page: 2585 year: 2008 end-page: 2588 publication-title: Org. Lett. – volume: 18 start-page: 4716 year: 2008 end-page: 4722 publication-title: Bioorg. Med. Chem. Lett. – volume: 447 start-page: 817 year: 2007 end-page: 822 publication-title: Nature – volume: 136 start-page: 9878 year: 2014 end-page: 9881 publication-title: J. Am. Chem. Soc. – volume: 136 start-page: 13202 year: 2014 end-page: 13208 publication-title: J. Am. Chem. Soc. – volume: 59 start-page: 2337 year: 2015 end-page: 2342 publication-title: Antimicrob. Agents Chemother. – volume: 53 start-page: 3331 year: 2009 end-page: 3336 publication-title: Antimicrob. Agents Chemother. – volume: 60 start-page: 2925 year: 1995 end-page: 2930 publication-title: J. Org. Chem. – volume: 193 start-page: 283 year: 1980 end-page: 292 publication-title: J. Organomet. Chem. – volume: 68 start-page: 2861 year: 2003 end-page: 2873 publication-title: J. Org. Chem. – volume: 61 start-page: 646 year: 2012 end-page: 664 publication-title: Gut – volume: 122 start-page: 2440 year: 2000 end-page: 2445 publication-title: J. Am. Chem. Soc. – volume: 291 start-page: 187 year: 2004 end-page: 194 publication-title: JAMA J. Am. Med. Assoc. – volume: 15 start-page: 6014 year: 2013 end-page: 6017 publication-title: Org. Lett. – volume: 19 start-page: 930 year: 2009 end-page: 936 publication-title: Bioorg. Med. Chem. Lett. – volume: 6 start-page: 209 year: 2004 end-page: 212 publication-title: Org. Lett. – volume: 61 start-page: 2885 year: 1996 end-page: 2887 publication-title: J. Org. Chem. – volume: 22 start-page: 5600 year: 2012 end-page: 5607 publication-title: Bioorg. Med. Chem. Lett. – volume: 105 start-page: 6177 year: 1983 end-page: 6178 publication-title: J. Am. Chem. Soc. – volume: 2 start-page: 1 year: 1991 end-page: 26 publication-title: Tetrahedron: Asymmetry – ident: e_1_2_2_28_1 doi: 10.1021/ja505131v – ident: e_1_2_2_20_2 doi: 10.1016/S0040-4020(01)81452-6 – ident: e_1_2_2_30_1 doi: 10.1021/jo0266339 – ident: e_1_2_2_33_1 doi: 10.1002/anie.201109221 – ident: e_1_2_2_5_1 doi: 10.1136/gutjnl-2012-302084 – ident: e_1_2_2_12_2 doi: 10.1016/j.bmcl.2012.07.004 – ident: e_1_2_2_13_2 doi: 10.1111/j.1751-7915.2008.00031.x – ident: e_1_2_2_1_1 – ident: e_1_2_2_40_1 – ident: e_1_2_2_42_2 doi: 10.1021/ol027447s – ident: e_1_2_2_19_2 doi: 10.1016/S0040-4039(00)81783-9 – ident: e_1_2_2_31_1 doi: 10.1016/S0040-4020(02)01089-X – ident: e_1_2_2_14_2 doi: 10.1128/AAC.04410-14 – ident: e_1_2_2_23_1 doi: 10.1021/ja984113i – ident: e_1_2_2_15_1 doi: 10.1021/ol800898z – ident: e_1_2_2_3_2 doi: 10.1111/j.1469-0691.2009.03031.x – ident: e_1_2_2_22_1 doi: 10.1021/jo951978v – ident: e_1_2_2_4_2 doi: 10.1001/jama.291.2.187 – ident: e_1_2_2_9_1 doi: 10.1038/nature05689 – ident: e_1_2_2_16_1 doi: 10.1039/P19940002137 – ident: e_1_2_2_29_1 doi: 10.1021/ja0002058 – ident: e_1_2_2_21_2 doi: 10.1016/S0040-4020(01)87872-8 – ident: e_1_2_2_44_2 doi: 10.1002/anie.201206558 – ident: e_1_2_2_34_1 doi: 10.1248/cpb.33.1305 – ident: e_1_2_2_35_1 doi: 10.1021/ja00233a026 – ident: e_1_2_2_37_1 doi: 10.1021/ol036157o – ident: e_1_2_2_24_1 doi: 10.1016/j.tetlet.2004.02.010 – ident: e_1_2_2_8_2 doi: 10.1016/j.bmcl.2008.11.113 – ident: e_1_2_2_33_2 doi: 10.1002/ange.201109221 – ident: e_1_2_2_7_2 doi: 10.1016/j.bmcl.2008.06.092 – ident: e_1_2_2_41_2 doi: 10.1016/S0957-4166(00)82150-3 – ident: e_1_2_2_18_1 – ident: e_1_2_2_11_1 – ident: e_1_2_2_38_1 doi: 10.1002/cctc.201300853 – ident: e_1_2_2_2_2 doi: 10.1038/nrc2857 – ident: e_1_2_2_27_1 doi: 10.1021/jo00114a054 – ident: e_1_2_2_17_1 doi: 10.1021/ol402905n – ident: e_1_2_2_10_1 doi: 10.1128/AAC.00226-09 – ident: e_1_2_2_43_2 doi: 10.1016/j.tet.2003.08.046 – ident: e_1_2_2_32_1 doi: 10.1021/ja5078188 – ident: e_1_2_2_25_1 doi: 10.1021/ol0526468 – ident: e_1_2_2_39_1 doi: 10.1021/ja00357a049 – ident: e_1_2_2_6_1 – ident: e_1_2_2_26_1 doi: 10.1016/S0022-328X(00)90287-0 – ident: e_1_2_2_44_3 doi: 10.1002/ange.201206558 – ident: e_1_2_2_36_1 doi: 10.1021/ja01043a041 – volume: 45 start-page: 2511 year: 2004 ident: WOS:000220150900006 article-title: An efficient synthesis of substituted anthraquinones and naphthoquinones publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2004.02.010 – volume: 10 start-page: 403 year: 2010 ident: WOS:000278024500011 article-title: Helicobacter pylori: gastric cancer and beyond publication-title: NATURE REVIEWS CANCER doi: 10.1038/nrc2857 – volume: 58 start-page: 8689 year: 2002 ident: WOS:000178684200005 article-title: Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone as a new, selective and neutral system for the facile conversion of alcohols, thiols and selenols to alkyl halides in the presence of halide ions publication-title: TETRAHEDRON – volume: 136 start-page: 13202 year: 2014 ident: WOS:000342328200033 article-title: Synthesis of a des-B-Ring Bryostatin Analogue Leads to an Unexpected Ring Expansion of the Bryolactone Core publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja5078188 – volume: 10 start-page: 2585 year: 2008 ident: WOS:000256762100065 article-title: Exiguaquinol: A novel pentacyclic hydroquinone from Neopetrosia exigua that inhibits Helicobacter pylori murl publication-title: ORGANIC LETTERS doi: 10.1021/ol800898z – volume: 46 start-page: 6851 year: 1990 ident: WOS:A1990EA74800024 article-title: PREPARATION OF FUNCTIONALIZED ANTHRA[B]CYCLOBUTENES FROM 3,6-DIMETHOXYBENZOCYCLOBUTENONE publication-title: TETRAHEDRON – volume: 22 start-page: 5600 year: 2012 ident: WOS:000308046400048 article-title: Design of inhibitors of Helicobacter pylori glutamate racemase as selective antibacterial agents: Incorporation of imidazoles onto a core pyrazolopyrimidinedione scaffold to improve bioavailabilty publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS doi: 10.1016/j.bmcl.2012.07.004 – volume: 6 start-page: 209 year: 2004 ident: WOS:000188297300017 article-title: Synthesis and protection of aryl sulfates using the 2,2,2-trichloroethyl moiety publication-title: ORGANIC LETTERS doi: 10.1021/ol036157o – volume: 68 start-page: 2861 year: 2003 ident: WOS:000181953700043 article-title: Scope and mechanism of palladium-catalyzed amination of five-membered heterocyclic halides publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo0266339 – volume: 19 start-page: 930 year: 2009 ident: WOS:000262707000083 article-title: Potent and selective inhibitors of Helicobacter pylori glutamate racemase (MurI): Pyridodiazepine amines publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS doi: 10.1016/j.bmcl.2008.11.113 – volume: 61 start-page: 646 year: 2012 ident: WOS:000302776700004 article-title: Management of Helicobacter pylori infection-the Maastricht IV/ Florence Consensus Report publication-title: GUT doi: 10.1136/gutjnl-2012-302084 – volume: 59 start-page: 2337 year: 2015 ident: WOS:000354993700060 article-title: Pyridodiazepine Amines Are Selective Therapeutic Agents for Helicobacter pylori by Suppressing Growth through Inhibition of Glutamate Racemase but Are Predicted To Require Continuous Elevated Levels in Plasma To Achieve Clinical Efficacy publication-title: ANTIMICROBIAL AGENTS AND CHEMOTHERAPY doi: 10.1128/AAC.04410-14 – volume: 447 start-page: 817 year: 2007 ident: WOS:000247207500035 article-title: Exploitation of structural and regulatory diversity in glutamate racemases publication-title: NATURE doi: 10.1038/nature05689 – volume: 60 start-page: 2925 year: 1995 ident: WOS:A1995QX16500054 article-title: SYNTHESIS OF ENANTIOMERICALLY PURE 4-SUBSTITUTED GLUTAMIC ACIDS AND PROLINES - GENERAL ALDOL REACTION OF PYROGLUTAMATE LACTAM LITHIUM ENOLATE MEDIATED BY ET(2)O-CENTER-DOT-BF3 publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 8 start-page: 273 year: 2006 ident: WOS:000234657900025 article-title: Syntheses of soluble, pi-stacking tetracene derivatives publication-title: ORGANIC LETTERS doi: 10.1021/ol0526468 – volume: 18 start-page: 4716 year: 2008 ident: WOS:000258769200061 article-title: Design of Helicobacter pylori glutamate racemase inhibitors as selective antibacterial agents: A novel pro-drug approach to increase exposure publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS doi: 10.1016/j.bmcl.2008.06.092 – volume: 5 start-page: 535 year: 2003 ident: WOS:000181077200039 article-title: Asymmetric total synthesis of the proposed structure of the medicinal alkaloid jamtine using the chiral base approach publication-title: ORGANIC LETTERS doi: 10.1021/ol027447s – volume: 1 start-page: 345 year: 2008 ident: WOS:000207904700004 article-title: Glutamate racemase as a target for drug discovery publication-title: MICROBIAL BIOTECHNOLOGY doi: 10.1111/j.1751-7915.2008.00031.x – start-page: 2137 year: 1994 ident: WOS:A1994PC00500019 article-title: STEREOCHEMISTRY OF CONVERSION OF THE SUICIDE SUBSTRATES BETA-CHLORO-D-ALANINE AND D-SERINE AND L-SERINE O-SULFATES INTO PYRUVATE BY D-AMINO-ACID AMINOTRANSFERASE AND BY L-ASPARTATE AMINOTRANSFERASE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 – volume: 15 start-page: 971 year: 2009 ident: WOS:000271055600003 article-title: Helicobacter pylori and gastric adenocarcinoma publication-title: CLINICAL MICROBIOLOGY AND INFECTION doi: 10.1111/j.1469-0691.2009.03031.x – volume: 51 start-page: 2505 year: 2012 ident: WOS:000300934700044 article-title: Total Syntheses of All the Amathaspiramides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201109221 – volume: 2 start-page: 1 year: 1991 ident: WOS:A1991EX89500001 article-title: ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES publication-title: TETRAHEDRON-ASYMMETRY – volume: 51 start-page: 12068 year: 2012 ident: WOS:000311705000028 article-title: Chiral Bases as Useful Probes of Lithium Amide Reactivity publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201206558 – volume: 59 start-page: 9213 year: 2003 ident: WOS:000186311700018 article-title: Application of the chiral base desymmetrisation of imides to the synthesis of the alkaloid jamtine and the antidepressant paroxetine publication-title: TETRAHEDRON doi: 10.1016/j.tet.2003.08.046 – volume: 53 start-page: 3331 year: 2009 ident: WOS:000268098300022 article-title: Pyrazolopyrimidinediones Are Selective Agents for Helicobacter pylori That Suppress Growth through Inhibition of Glutamate Racemase (MurI) publication-title: ANTIMICROBIAL AGENTS AND CHEMOTHERAPY doi: 10.1128/AAC.00226-09 – volume: 110 start-page: 8483 year: 1988 ident: WOS:A1988R339800026 article-title: TOTAL SYNTHESIS OF (+)-HALENAQUINOL AND (+)-HALENAQUINONE - EXPERIMENTAL PROOF OF THEIR ABSOLUTE STEREOSTRUCTURES THEORETICALLY DETERMINED publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 136 start-page: 9878 year: 2014 ident: WOS:000339228200021 article-title: Design, Development, Mechanistic Elucidation, and Rational Optimization of a Tandem Ireland Claisen/Cope Rearrangement Reaction for Rapid Access to the (Iso)Cyclocitrinol Core publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja505131v – volume: 33 start-page: 1305 year: 1985 ident: WOS:A1985AFD6700059 article-title: HALENAQUINOL AND HALENAQUINOL SULFATE, PENTACYCLIC HYDROQUINONES FROM THE OKINAWAN MARINE SPONGE XESTOSPONGIA-SAPRA publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN – volume: 24 start-page: 1829 year: 1983 ident: WOS:A1983QM55700022 article-title: 3,6-DIMETHOXYBENZOCYCLOBUTENONE - A VERSATILE QUINONE PRECURSOR publication-title: TETRAHEDRON LETTERS – volume: 6 start-page: 1059 year: 2014 ident: WOS:000334180500025 article-title: Aryl Sulfotransferase from Haliangium ochraceum: A Versatile Tool for the Sulfation of Small Molecules publication-title: CHEMCATCHEM doi: 10.1002/cctc.201300853 – volume: 124 start-page: 2555 year: 2012 ident: 000390604600012.13 publication-title: Angew. Chem. – volume: 105 start-page: 6177 year: 1983 ident: WOS:A1983RH32900049 article-title: HALENAQUINONE, A PENTACYCLIC POLYKETIDE FROM A MARINE SPONGE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 193 start-page: 283 year: 1980 ident: WOS:A1980KB25700001 article-title: THE SYNTHESIS AND REACTIONS OF ORTHO-BROMOPHENYLLITHIUM publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY – volume: 122 start-page: 2440 year: 2000 ident: WOS:000086057200005 article-title: Bond alternation in azulenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 124 start-page: 12234 year: 2012 ident: 000390604600012.36 publication-title: Angew. Chem. – volume: 61 start-page: 2885 year: 1996 ident: WOS:A1996UG48300053 article-title: Synthesis of functionalized naphthalenes from substituted 1-methoxybenzocyclobutenes publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 91 start-page: 4273 year: 1969 ident: WOS:A1969D665400041 article-title: PREPARATION OF SULFATE ESTERS . REACTIONS OF VARIOUS ALCOHOLS, PHENOLS, AMINES, MERCAPTANS, AND OXIMES WITH SULFURIC ACID AND DICYCLOHEXYLCARBODIIMIDE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 15 start-page: 6014 year: 2013 ident: WOS:000328231500028 article-title: Synthesis of the Tetracyclic Core of Exiguaquinol publication-title: ORGANIC LETTERS doi: 10.1021/ol402905n – volume: 122 start-page: 4020 year: 2000 ident: WOS:000086950500005 article-title: Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 291 start-page: 187 year: 2004 ident: WOS:000188040900026 article-title: Helicobacter pylori eradication to prevent gastric cancer in a high-risk region of China - A randomized controlled trial publication-title: JAMA-JOURNAL OF THE AMERICAN MEDICAL ASSOCIATION – volume: 44 start-page: 5939 year: 1988 ident: WOS:A1988Q441100028 article-title: 3,6-DIMETHOXYBENZOCYCLOBUTENONE - A REAGENT FOR QUINONE SYNTHESIS publication-title: TETRAHEDRON
SSID	ssj0009633
Score	2.2534482
Snippet	A concise and stereoselective synthesis of exiguaquinol dessulfate is described. Sequential application of a Diels–Alder cycloaddition, a desymmetrizing aldol... A concise and stereoselective synthesis of exiguaquinol dessulfate is described. Sequential application of a Diels-Alder cycloaddition, a desymmetrizing aldol...
Source	Web of Science
SourceID	pubmedcentral proquest pubmed webofscience crossref wiley istex
SourceType	Open Access Repository Aggregation Database Index Database Enrichment Source Publisher
StartPage	17953
SubjectTerms	Aldehydes Aldehydes - chemistry antibiotics Architecture Chemistry Chemistry, Multidisciplinary Congeners Culture Cyclization Cycloaddition Reaction epimers Forges Heck cyclization Hydrogen bonding Hydroquinones - chemical synthesis Hydroquinones - chemistry Molecular Structure natural product synthesis Physical Sciences Science & Technology Strategy sulfation Synthesis
Title	A Synthesis of Exiguaquinol Dessulfate
URI	https://api.istex.fr/ark:/67375/WNG-1D97VSKG-C/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.201604506 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000390604600012 https://www.ncbi.nlm.nih.gov/pubmed/27673578 https://www.proquest.com/docview/1848809146 https://www.proquest.com/docview/1835686824 https://www.proquest.com/docview/1864568332 https://pubmed.ncbi.nlm.nih.gov/PMC6028001
Volume	22
WOS	000390604600012
WOSCitedRecordID	wos000390604600012
hasFullText	1
inHoldings	1
isFullTextHit
isPrint
journalDatabaseRights	– providerCode: PRVWIB databaseName: Wiley Online Library Full Collection 2020 customDbUrl: eissn: 1521-3765 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0009633 issn: 0947-6539 databaseCode: DRFUL dateStart: 19980101 isFulltext: true titleUrlDefault: https://onlinelibrary.wiley.com providerName: Wiley-Blackwell
link	http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV3db9MwED9Bi8Re-GYExhSkaTxFq-3ETh6ndh0SqEKMQd8sf0JElULTovHfYyept0jjQ_CWyOcod77z3fnjdwAHguYjkUqRKCbSJE21TKQyRVLoXFMmdIa1bIpNsNksn8-Lt1du8bf4EGHBzVtGM197AxeyProEDXU8-ZvkiLqgxGNuD7FT3mwAw8m76fmbS-Bd2pWTT1niYVi3wI0jfNT_Qs8xDb2ML66LOq8_PBkcVj_GbZzU9O7_s3cP7nQBanzcatR9uGGqB3B7vK0L9xAOj-OzH5WLG-uyjpc2PrkoP23Et01ZLRfxxCfvC-sC2EdwPj15P36VdNUWEuVyEJrglFhn7AZbi7SwCBvnxxRzM2JGc00EkVJlVFJDjElVjokbYsuU0bZQLva15DEMqmVlnkCMFDGZtAVRyiVgEomskGJkaIa040abCJKtqLnqoMh9RYwFb0GUMffc88B9BC8D_dcWhOOXlIfNyAUysfrij66xjH-cnXI0KdiHs9enfBzB3nZoeWe1NXfZrpvOCuc8IngRmp14_SaKqMxy42m8PGiO09_RUBeX5oTgCHZbbQk_hJn7HTdNRsB6ehQIPN53v6UqPze439Rvg49QBAdXNS50bO5Zeywk2iwvRoD-hmzcyd9DIKwjwI1O_kHK3MN1hLen_9LpGez4Z38wCOE9GKxXG_Mcbqnv67Je7cNNNs_3O1P-CcM5R3I
linkProvider	Wiley-Blackwell
linkToHtml	http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV3db9QwDLfQDmm8AONjFMYo0jSeql2TNmkfp7vdhnacENtgb1GaJlBx6sF9oPHfY7e9jkrjQ4jHNk5VO3Zs5-NngD0tkr6OMh0YqaMgivIsyIxNgzRPciF1HrM8q4pNyMkkubxM3zanCekuTI0P0S64kWVU8zUZOC1IH1yjhiJTdJU8FBiVEOh2L0JdQiXvDd-NLsbXyLuiqScfyYBwWNfIjX120P1CxzP1SMhXN4WdN5-ebD1WN8itvNTo3n_g7z7cbUJU_7DWqS24ZcsHsDlYV4Z7CPuH_tn3EiPHRbHwZ84_uio-rvTXVVHOpv6Q0vepwxD2EVyMjs4HJ0FTbyEwmIWIgEXcoblb5lyYaxcyi57MSJwTY5HkXPMsM7HIhOXWRiZhHAfZSWNzlxqMfh1_DBvlrLRPwA8Nt3HmUm4MpmBZqOM0030r4jBHbnLrQbCWtTINGDnVxJiqGkaZKeJetdx78Kql_1LDcPyScr8aupZMzz_T4TUZqw-TYxUOU_n-7PRYDTzYWY-taux2oTDfxQktRffhwcu2GcVL2yi6tLMV0ZA8RMKi39EIjEwTzpkH27W6tD_EJP4OTpQeyI4itQSE-N1tKYtPFfK3oI3wfujB3s8q13asbloTGpKoFhg9CP-GbNDIn0AQlh6wSin_IGVFgB3t09N_6fQCNk_O34zV-PXk9Bncofd0TChkO7CxnK_sc7htvi2LxXy3segfm99Keg
linkToPdf	http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV1Zb9QwEB6hXQS8cB-BAkGqylPUtZ3YyWO12y2o1aqiFPpm-YSIVbbsgcq_x5NkU1YqhxCPicdRZjzjmfHxDcC24vlApVolRqg0SVOrE21ckRQ2t1wom1Gr62ITYjLJz86K4_Y0Id6FafAhugU3tIx6vkYDd-fW716ihgam8Co54SEqQdDtfoqVZHrQH70bnx5dIu_ytp58KhLEYV0jNw7o7uYXNjxTH4V8cVXYefXpyc5jbQa5tZca3_kP_N2F222IGu81OnUPrrnqPtwcrivDPYCdvfjkexUix0W5iGc-3r8oP63U11VZzabxCNP3qQ8h7EM4He-_H75J2noLiQlZCE9oynwwd0e9J1Z5Ql3wZEaEOTHjuWWKaW0yrrljzqUmpywMshfGWV-YEP169gh61axyTyAmhrlM-4IZE1IwTVRWaDVwPCM2cGNdBMla1tK0YORYE2MqGxhlKpF72XEfweuO_ryB4fgl5U49dB2Zmn_Bw2sikx8nB5KMCvHh5PBADiPYWo-tbO12IUO-Gya0IriPCF51zUG8uI2iKjdbIQ3Kg-c0_R0ND5FpzhiN4HGjLt0PURF-J0yUEYgNReoIEPF7s6UqP9fI3xw3wgckgu2fVa7rWN-0RjQkXi8wRkD-hmzYyh9BEJYR0Fop_yBliYAd3dPTf-n0Em4cj8by6O3k8Bncwtd4SojQLegt5yv3HK6bb8tyMX_RGvQPuk9J9Q
openUrl	ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=A+Synthesis+of+Exiguaquinol+Dessulfate&rft.jtitle=Chemistry+%3A+a+European+journal&rft.au=Schwarzwalder%2C+Gregg+M&rft.au=Scott%2C+David+R&rft.au=Vanderwal%2C+Christopher+D&rft.date=2016-12-12&rft.issn=0947-6539&rft.eissn=1521-3765&rft.volume=22&rft.issue=50&rft.spage=17953&rft.epage=17957&rft_id=info:doi/10.1002%2Fchem.201604506&rft.externalDBID=NO_FULL_TEXT
thumbnail_l	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0947-6539&client=summon
thumbnail_m	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0947-6539&client=summon
thumbnail_s	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0947-6539&client=summon