Asymmetric Synthesis of Tetracyclic Pyrroloindolines and Constrained Tryptamines by a Switchable Cascade Reaction

The interrupted Fischer indole synthesis of arylhydrazines and biocatalytically generated chiral bicyclic imines selectively affords either tetracyclic pyrroloindolines or tricyclic tryptamine analogues depending on the reaction conditions. We demonstrate that the reaction is compatible with a varie...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Angewandte Chemie Jg. 127; H. 47; S. 14339 - 14342
Hauptverfasser:	de Graaff, Corien, Bensch, Lisa, Boersma, Sjoerd J., Cioc, Răzvan C., van Lint, Matthijs J., Janssen, Elwin, Turner, Nicholas J., Orru, Romano V. A., Ruijter, Eelco
Format:	Journal Article
Sprache:	Englisch Deutsch
Veröffentlicht:	Weinheim WILEY‐VCH Verlag 16.11.2015 Wiley Subscription Services, Inc
Schlagworte:	Asymmetric synthesis Asymmetrische Synthesen Asymmetry Biologisch aktive Verbindungen Capsaicin receptors Cascade chemical reactions Chemistry Cholinesterase Cholinesterase inhibitors Constraints Derivatives Functional groups Imines Indoles Inhibitors Ion channels Reaction mechanisms Reaktionskaskaden Serotonin Stoichiometry Synthesemethoden Synthesis (chemistry) Tryptamine Tryptamines
ISSN:	0044-8249, 1521-3757
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Abstract	The interrupted Fischer indole synthesis of arylhydrazines and biocatalytically generated chiral bicyclic imines selectively affords either tetracyclic pyrroloindolines or tricyclic tryptamine analogues depending on the reaction conditions. We demonstrate that the reaction is compatible with a variety of functional groups. The products are obtained in high optical purity and in reasonable to good yield. We present a plausible reaction mechanism to explain the observed reaction outcome depending on the stoichiometry of the acid mediator. To demonstrate the synthetic utility of our method, pharmaceutically relevant examples of both product classes were synthesized in highly efficient reaction sequences, including a phenserine analogue as a potential cholinesterase inhibitor and constrained tryptamine derivatives as selective inhibitors of the 5‐HT6 serotonin receptor and the TRPV1 ion channel. Am Scheideweg: Unterbrochene Fischer‐Indolsynthesen mit Arylhydrazinen und chiralen bicyclischen Iminen ergeben abhängig von den Reaktionsbedingungen selektiv entweder tetracyclische Pyrroloindoline oder tricyclische Tryptamin‐Analoga. Die optisch hoch reinen Produkte lassen sich leicht in medizinisch bedeutende Verbindungen umsetzen.
AbstractList	The interrupted Fischer indole synthesis of arylhydrazines and biocatalytically generated chiral bicyclic imines selectively affords either tetracyclic pyrroloindolines or tricyclic tryptamine analogues depending on the reaction conditions. We demonstrate that the reaction is compatible with a variety of functional groups. The products are obtained in high optical purity and in reasonable to good yield. We present a plausible reaction mechanism to explain the observed reaction outcome depending on the stoichiometry of the acid mediator. To demonstrate the synthetic utility of our method, pharmaceutically relevant examples of both product classes were synthesized in highly efficient reaction sequences, including a phenserine analogue as a potential cholinesterase inhibitor and constrained tryptamine derivatives as selective inhibitors of the 5-HT sub(6) serotonin receptor and the TRPV1 ion channel.Original Abstract: Am Scheideweg: Unterbrochene Fischer-Indolsynthesen mit Arylhydrazinen und chiralen bicyclischen Iminen ergeben abhaengig von den Reaktionsbedingungen selektiv entweder tetracyclische Pyrroloindoline oder tricyclische Tryptamin-Analoga. Die optisch hoch reinen Produkte lassen sich leicht in medizinisch bedeutende Verbindungen umsetzen. The interrupted Fischer indole synthesis of arylhydrazines and biocatalytically generated chiral bicyclic imines selectively affords either tetracyclic pyrroloindolines or tricyclic tryptamine analogues depending on the reaction conditions. We demonstrate that the reaction is compatible with a variety of functional groups. The products are obtained in high optical purity and in reasonable to good yield. We present a plausible reaction mechanism to explain the observed reaction outcome depending on the stoichiometry of the acid mediator. To demonstrate the synthetic utility of our method, pharmaceutically relevant examples of both product classes were synthesized in highly efficient reaction sequences, including a phenserine analogue as a potential cholinesterase inhibitor and constrained tryptamine derivatives as selective inhibitors of the 5‐HT 6 serotonin receptor and the TRPV1 ion channel. The interrupted Fischer indole synthesis of arylhydrazines and biocatalytically generated chiral bicyclic imines selectively affords either tetracyclic pyrroloindolines or tricyclic tryptamine analogues depending on the reaction conditions. We demonstrate that the reaction is compatible with a variety of functional groups. The products are obtained in high optical purity and in reasonable to good yield. We present a plausible reaction mechanism to explain the observed reaction outcome depending on the stoichiometry of the acid mediator. To demonstrate the synthetic utility of our method, pharmaceutically relevant examples of both product classes were synthesized in highly efficient reaction sequences, including a phenserine analogue as a potential cholinesterase inhibitor and constrained tryptamine derivatives as selective inhibitors of the 5-HT6 serotonin receptor and the TRPV1 ion channel. The interrupted Fischer indole synthesis of arylhydrazines and biocatalytically generated chiral bicyclic imines selectively affords either tetracyclic pyrroloindolines or tricyclic tryptamine analogues depending on the reaction conditions. We demonstrate that the reaction is compatible with a variety of functional groups. The products are obtained in high optical purity and in reasonable to good yield. We present a plausible reaction mechanism to explain the observed reaction outcome depending on the stoichiometry of the acid mediator. To demonstrate the synthetic utility of our method, pharmaceutically relevant examples of both product classes were synthesized in highly efficient reaction sequences, including a phenserine analogue as a potential cholinesterase inhibitor and constrained tryptamine derivatives as selective inhibitors of the 5‐HT6 serotonin receptor and the TRPV1 ion channel. Am Scheideweg: Unterbrochene Fischer‐Indolsynthesen mit Arylhydrazinen und chiralen bicyclischen Iminen ergeben abhängig von den Reaktionsbedingungen selektiv entweder tetracyclische Pyrroloindoline oder tricyclische Tryptamin‐Analoga. Die optisch hoch reinen Produkte lassen sich leicht in medizinisch bedeutende Verbindungen umsetzen.
Author	Bensch, Lisa Ruijter, Eelco Turner, Nicholas J. de Graaff, Corien Orru, Romano V. A. van Lint, Matthijs J. Cioc, Răzvan C. Boersma, Sjoerd J. Janssen, Elwin
Author_xml	– sequence: 1 givenname: Corien surname: de Graaff fullname: de Graaff, Corien – sequence: 2 givenname: Lisa surname: Bensch fullname: Bensch, Lisa – sequence: 3 givenname: Sjoerd J. surname: Boersma fullname: Boersma, Sjoerd J. – sequence: 4 givenname: Răzvan C. surname: Cioc fullname: Cioc, Răzvan C. – sequence: 5 givenname: Matthijs J. surname: van Lint fullname: van Lint, Matthijs J. – sequence: 6 givenname: Elwin surname: Janssen fullname: Janssen, Elwin – sequence: 7 givenname: Nicholas J. surname: Turner fullname: Turner, Nicholas J. – sequence: 8 givenname: Romano V. A. surname: Orru fullname: Orru, Romano V. A. – sequence: 9 givenname: Eelco surname: Ruijter fullname: Ruijter, Eelco email: e.ruijter@vu.nl
BookMark	eNqFkcFrHCEUxqWk0E2aa89CL73M9unojh6XJU0LoQnN9iyOOo3B0Y3OEua_r5stKQTSnuT5ft_jve87RScxRYfQBwJLAkA_6_jLLSkQDh0w8gYtCKekaTvenaAFAGONoEy-Q6el3APAinZygR7WZR5HN2Vv8O0cpztXfMFpwNv6p81sQm3czDmnkHy0KfjoCtbR4k2KpSK1tnib592kx6deP2ONbx_9ZO50Hxze6GK0dfiH02byKb5Hbwcdijv_856hn18utpuvzdX15bfN-qoxlLakEYPkXb9yWmjbMklJD4QROUhbz-vbFqiW1q2IlZQOzgjSDkAtCM60sb3s2jP06Th3l9PD3pVJjb4YF4KOLu2LIqJ6IqjoeEU_vkDv0z7Hup2ifEUJg5bLf1GkmgyccCkqxY6UyamU7AZl_KQPhx_MCoqAOqSlDmmp57SqbPlCtst-1Hl-XSCPgkcf3PwfWq2_X1781f4GBrKp7Q
CitedBy_id	crossref_primary_10_1002_adsc_202101232 crossref_primary_10_1002_adsc_201600038 crossref_primary_10_1002_anie_202210592 crossref_primary_10_1002_ejoc_202101545 crossref_primary_10_1002_ajoc_202300594 crossref_primary_10_1002_ange_202210592 crossref_primary_10_1002_chem_201703890 crossref_primary_10_1002_adsc_202201168 crossref_primary_10_1002_chem_201601560
Cites_doi	10.1002/ange.201001592 10.1002/ange.200906655 10.1002/ange.200901843 10.1021/jo051387x 10.1002/ange.201007004 10.1002/chem.201202908 10.1002/ange.201301618 10.1002/anie.201301618 10.1021/ol901383j 10.1021/ol052403f 10.1039/c0cc02823a 10.1021/ja01626a037 10.1016/j.bmcl.2007.12.007 10.1002/ange.201107677 10.1021/ja203227q 10.1016/S0960-894X(01)80566-7 10.1002/anie.200906655 10.1002/anie.201001592 10.1002/anie.200901843 10.1021/jo202078z 10.1038/nchembio.758 10.1517/13543784.16.7.1087 10.1002/anie.201007004 10.1038/nchem.1297 10.1016/j.bmcl.2006.12.089 10.1002/anie.201107677
ContentType	Journal Article
Copyright	2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright Wiley Subscription Services, Inc. Nov 2015
Copyright_xml	– notice: 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim – notice: 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim – notice: Copyright Wiley Subscription Services, Inc. Nov 2015
DBID	AAYXX CITATION 7SR 7U5 8BQ 8FD JG9 L7M
DOI	10.1002/ange.201507041
DatabaseName	CrossRef Engineered Materials Abstracts Solid State and Superconductivity Abstracts METADEX Technology Research Database Materials Research Database Advanced Technologies Database with Aerospace
DatabaseTitle	CrossRef Materials Research Database Engineered Materials Abstracts Solid State and Superconductivity Abstracts Technology Research Database Advanced Technologies Database with Aerospace METADEX
DatabaseTitleList	Materials Research Database CrossRef Materials Research Database Materials Research Database
DeliveryMethod	fulltext_linktorsrc
Discipline	Chemistry
EISSN	1521-3757
EndPage	14342
ExternalDocumentID	3922243781 10_1002_ange_201507041 ANGE201507041
Genre	shortCommunication
GrantInformation_xml	– fundername: Royal Society – fundername: Netherlands Organization for Scientific Research (NWO) – fundername: NSF funderid: 1337296
GroupedDBID	-~X .3N .GA 05W 0R~ 10A 1L6 1OB 1OC 1ZS 33P 3SF 3WU 4.4 50Y 50Z 51W 51X 52M 52N 52O 52P 52S 52T 52U 52W 52X 5VS 66C 6P2 702 7PT 8-0 8-1 8-3 8-4 8-5 8UM 930 A03 AAESR AAEVG AAHHS AAHQN AAMNL AANLZ AAONW AASGY AAXRX AAYCA AAZKR ABCQN ABCUV ABDBF ABEML ABIJN ABJNI ABLJU ABPVW ACAHQ ACBWZ ACCFJ ACCUC ACCZN ACGFS ACIWK ACNCT ACPOU ACPRK ACSCC ACUHS ACXBN ACXQS ACYXJ ADBBV ADEOM ADIZJ ADKYN ADMGS ADOZA ADXAS ADZMN ADZOD AEEZP AEIGN AEIMD AEQDE AEUQT AEUYR AFBPY AFFPM AFGKR AFPWT AFRAH AFWVQ AHBTC AITYG AIURR AIWBW AJBDE AJXKR ALAGY ALMA_UNASSIGNED_HOLDINGS ALUQN ALVPJ AMBMR AMYDB ATUGU AUFTA AZBYB AZVAB BAFTC BFHJK BHBCM BMNLL BMXJE BNHUX BROTX BRXPI BY8 CS3 D-E D-F DCZOG DPXWK DR2 DRFUL DRSTM EBS EJD F00 F01 F04 F5P G-S G.N GNP GODZA H.T H.X HGLYW HHY HHZ HZ~ IX1 J0M JPC KQQ LATKE LAW LC2 LC3 LEEKS LITHE LOXES LP6 LP7 LUTES LYRES MEWTI MK4 MRFUL MRSTM MSFUL MSSTM MXFUL MXSTM N04 N05 N9A NF~ O66 O9- OIG P2W P2X P4D Q.N Q11 QB0 QRW R.K RGC ROL RWI RX1 RYL SUPJJ TN5 TUS UB1 UPT V2E W8V W99 WBFHL WBKPD WIH WIK WJL WOHZO WQJ WRC WXSBR WYISQ XG1 XV2 Y6R ZZTAW ~IA ~WT AAMMB AAYXX AEFGJ AEYWJ AGQPQ AGXDD AGYGG AIDQK AIDYY CITATION O8X 7SR 7U5 8BQ 8FD JG9 L7M
ID	FETCH-LOGICAL-c2231-8f957b6ea8ad34921b01419f9d070b3302a9de61d922fec813f02d0854acdb973
IEDL.DBID	DRFUL
ISSN	0044-8249
IngestDate	Thu Oct 02 03:54:31 EDT 2025 Fri Jul 25 10:42:24 EDT 2025 Sun Jul 13 05:17:25 EDT 2025 Sat Nov 29 03:22:07 EST 2025 Tue Nov 18 21:59:34 EST 2025 Wed Jan 22 16:34:44 EST 2025
IsPeerReviewed	true
IsScholarly	true
Issue	47
Language	English German
License	http://onlinelibrary.wiley.com/termsAndConditions#vor
LinkModel	DirectLink
MergedId	FETCHMERGED-LOGICAL-c2231-8f957b6ea8ad34921b01419f9d070b3302a9de61d922fec813f02d0854acdb973
Notes	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
PQID	1757051598
PQPubID	866336
PageCount	4
ParticipantIDs	proquest_miscellaneous_1800482875 proquest_journals_2562140359 proquest_journals_1757051598 crossref_citationtrail_10_1002_ange_201507041 crossref_primary_10_1002_ange_201507041 wiley_primary_10_1002_ange_201507041_ANGE201507041
PublicationCentury	2000
PublicationDate	November 16, 2015
PublicationDateYYYYMMDD	2015-11-16
PublicationDate_xml	– month: 11 year: 2015 text: November 16, 2015 day: 16
PublicationDecade	2010
PublicationPlace	Weinheim
PublicationPlace_xml	– name: Weinheim
PublicationTitle	Angewandte Chemie
PublicationYear	2015
Publisher	WILEY‐VCH Verlag Wiley Subscription Services, Inc
Publisher_xml	– name: WILEY‐VCH Verlag – name: Wiley Subscription Services, Inc
References	2007; 17 2009; 11 2010; 46 2009 2009; 48 121 2008; 18 2012 2012; 51 124 2006; 8 2010 2010; 49 122 2012; 18 2011 2011; 50 123 2005; 70 1955 2012; 77 4 2012; 77 2011; 133 1994; 4 2012; 8 2013 2013; 52 125 2007; 16 e_1_2_4_20_2 e_1_2_4_22_2 e_1_2_4_21_2 e_1_2_4_24_2 e_1_2_4_23_2 e_1_2_4_26_2 e_1_2_4_25_2 e_1_2_4_28_2 e_1_2_4_27_2 e_1_2_4_29_3 e_1_2_4_29_2 e_1_2_4_1_3 e_1_2_4_2_2 e_1_2_4_1_2 e_1_2_4_4_2 e_1_2_4_3_2 e_1_2_4_6_2 e_1_2_4_4_3 e_1_2_4_5_2 e_1_2_4_8_2 e_1_2_4_6_3 e_1_2_4_7_2 e_1_2_4_8_3 e_1_2_4_9_2 e_1_2_4_10_2 e_1_2_4_11_2 e_1_2_4_12_2 e_1_2_4_13_2 e_1_2_4_13_3 e_1_2_4_14_2 e_1_2_4_15_2 e_1_2_4_16_3 e_1_2_4_17_2 e_1_2_4_16_2 e_1_2_4_19_2 e_1_2_4_18_2
References_xml	– volume: 16 start-page: 1087 year: 2007 publication-title: Expert Opin. Invest. Drugs – volume: 77 start-page: 725 year: 2012 publication-title: J. Org. Chem. – volume: 17 start-page: 1691 year: 2007 publication-title: Bioorg. Med. Chem. Lett. – volume: 18 start-page: 1072 year: 2008 publication-title: Bioorg. Med. Chem. Lett. – volume: 11 start-page: 3458 year: 2009 publication-title: Org. Lett. – volume: 46 start-page: 7918 year: 2010 publication-title: Chem. Commun. – volume: 8 start-page: 43 year: 2006 publication-title: Org. Lett. – volume: 52 125 start-page: 9486 9664 year: 2013 2013 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 18 start-page: 13250 year: 2012 publication-title: Chem. Eur. J. – volume: 49 122 start-page: 2182 2228 year: 2010 2010 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 49 122 start-page: 5289 5417 year: 2010 2010 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 48 121 start-page: 9608 9786 year: 2009 2009 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 8 start-page: 179 year: 2012 publication-title: Nat. Chem. Biol. – volume: 77 4 start-page: 5562 366 year: 1955 2012 publication-title: J. Am. Chem. Soc. Nat. Chem. – volume: 70 start-page: 8631 year: 2005 publication-title: J. Org. Chem. – volume: 133 start-page: 8877 year: 2011 publication-title: J. Am. Chem. Soc. – volume: 4 start-page: 1559 year: 1994 publication-title: Bioorg. Med. Chem. Lett. – volume: 51 124 start-page: 1680 1712 year: 2012 2012 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 50 123 start-page: 10800 10990 year: 2011 2011 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – ident: e_1_2_4_6_3 doi: 10.1002/ange.201001592 – ident: e_1_2_4_4_3 doi: 10.1002/ange.200906655 – ident: e_1_2_4_8_3 doi: 10.1002/ange.200901843 – ident: e_1_2_4_22_2 doi: 10.1021/jo051387x – ident: e_1_2_4_1_3 doi: 10.1002/ange.201007004 – ident: e_1_2_4_28_2 – ident: e_1_2_4_5_2 – ident: e_1_2_4_26_2 doi: 10.1002/chem.201202908 – ident: e_1_2_4_13_3 doi: 10.1002/ange.201301618 – ident: e_1_2_4_13_2 doi: 10.1002/anie.201301618 – ident: e_1_2_4_3_2 – ident: e_1_2_4_10_2 doi: 10.1021/ol901383j – ident: e_1_2_4_9_2 – ident: e_1_2_4_21_2 doi: 10.1021/ol052403f – ident: e_1_2_4_7_2 doi: 10.1039/c0cc02823a – ident: e_1_2_4_16_2 doi: 10.1021/ja01626a037 – ident: e_1_2_4_25_2 doi: 10.1016/j.bmcl.2007.12.007 – ident: e_1_2_4_29_3 doi: 10.1002/ange.201107677 – ident: e_1_2_4_11_2 doi: 10.1021/ja203227q – ident: e_1_2_4_24_2 doi: 10.1016/S0960-894X(01)80566-7 – ident: e_1_2_4_27_2 – ident: e_1_2_4_4_2 doi: 10.1002/anie.200906655 – ident: e_1_2_4_6_2 doi: 10.1002/anie.201001592 – ident: e_1_2_4_18_2 – ident: e_1_2_4_8_2 doi: 10.1002/anie.200901843 – ident: e_1_2_4_12_2 doi: 10.1021/jo202078z – ident: e_1_2_4_2_2 doi: 10.1038/nchembio.758 – ident: e_1_2_4_19_2 doi: 10.1517/13543784.16.7.1087 – ident: e_1_2_4_1_2 doi: 10.1002/anie.201007004 – ident: e_1_2_4_20_2 – ident: e_1_2_4_15_2 – ident: e_1_2_4_16_3 doi: 10.1038/nchem.1297 – ident: e_1_2_4_23_2 doi: 10.1016/j.bmcl.2006.12.089 – ident: e_1_2_4_14_2 – ident: e_1_2_4_17_2 – ident: e_1_2_4_29_2 doi: 10.1002/anie.201107677
SSID	ssj0006279
Score	1.9294819
Snippet	The interrupted Fischer indole synthesis of arylhydrazines and biocatalytically generated chiral bicyclic imines selectively affords either tetracyclic...
SourceID	proquest crossref wiley
SourceType	Aggregation Database Enrichment Source Index Database Publisher
StartPage	14339
SubjectTerms	Asymmetric synthesis Asymmetrische Synthesen Asymmetry Biologisch aktive Verbindungen Capsaicin receptors Cascade chemical reactions Chemistry Cholinesterase Cholinesterase inhibitors Constraints Derivatives Functional groups Imines Indoles Inhibitors Ion channels Reaction mechanisms Reaktionskaskaden Serotonin Stoichiometry Synthesemethoden Synthesis (chemistry) Tryptamine Tryptamines
Title	Asymmetric Synthesis of Tetracyclic Pyrroloindolines and Constrained Tryptamines by a Switchable Cascade Reaction
URI	https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fange.201507041 https://www.proquest.com/docview/1757051598 https://www.proquest.com/docview/2562140359 https://www.proquest.com/docview/1800482875
Volume	127
hasFullText	1
inHoldings	1
isFullTextHit
isPrint
journalDatabaseRights	– providerCode: PRVWIB databaseName: Wiley Online Library Full Collection 2020 customDbUrl: eissn: 1521-3757 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0006279 issn: 0044-8249 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/eLvHCXMwpV1La9tAEB6KU2gvfZe4TcsWCj2JaFdrSXs0btweggmJU3IT-wRDLKeSk6B_3xlJVhJoKbQ3SbMS-5jd-XY18w3AZyWy1FguI8PjEMmg8kinGUUsc8mVQZPbHrj9OM4Wi_ziQp3ci-Lv-CGGAzeaGe16TRNcm_rwjjSUfO_JNQsBTUyR63sClXcygr2vp_Pz42E1TkXHtxdLiRWQakfcGIvDh194aJju0OZ9zNoanfnz_6_uC3jWA0427TTkJTzy5St4MtvleXsNP6d1s15TYi3LzpoSAWG9qtkmsCU-07axlyg4aaoKl0ncwFOSH18zXTpGyT7bFBPesWXVXG31upWZhml2drtChaDALDbTNXnhs1PfRVG8gfP50XL2PeoTMUQW0QOP8qAmmUm9zrUjNkNuyD1UBeWwMSZJYqGV8yl3Sojgbc6TEAuHYE5q64zKkrcwKjel3wdmcmfQBKZJmnjcK2XKSC6DUUFLI7BjxhDtRqGwPUs5teSy6PiVRUEdWQwdOYYvQ_mrjp_jjyUPdoNa9PO0LhA8ZZTlRuW_FSMeFERoOFFj-DSIcXzor4ou_eYaP5HTKogbz8kYRKsBf6lIMV18Oxru3v3LS-_hKV1TTCRPD2C0ra79B3hsb7aruvrYT4FfzDgGCA
linkProvider	Wiley-Blackwell
linkToHtml	http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV3dS9xAEF-KFuxLtbal50e7BaFPwexmL8k-HqenpddD9Cy-hf2EAy-nyankv3cmyUWFlkLpY3Y3YT9mZn-7mfkNIQeSJ7E2TASahT4QXqaBihOMWGaCSQ1bbn3h9mucTCbp1ZU8a70JMRam4YfoLtxQM2p7jQqOF9KHT6yh6HyPvlmAaEIMXV8XIEsg5OtH56PLcWeOY94Q7oVCQA-EXDE3hvzw5Rde7kxPcPM5aK13ndHmf-jvFnnbQk46aGTkHXnl8m2yMVxlentPbgdlNZ9jai1DL6ocIGE5K-nC0ymUKVOZa6g4q4oCDCUc4THNjyupyi3FdJ91kgln6bSobpZqXtfpiip68TADkcDQLDpUJfrh03PXxFF8IJej4-nwNGhTMQQG8AMLUi_7iY6dSpVFPkOm0UFUemlhMDqKQq6kdTGzknPvTMoiH3ILcE4oY7VMoo9kLV_k7hOhOrUaNsE4iiMHp6VEasGE19IroTlMTI8Eq2XITMtTjiO5zhqGZZ7hRGbdRPbIt679TcPQ8ceWe6tVzVpNLTOATwnmuZHpb6sBEXKkNOzLHvnaVcP64H8VlbvFHXwiRTsIR89-j_BaBP7SkWwwOTnunnb-5aUvZON0-nOcjb9PfuySN1iOEZIs3iNry-LO7ZPX5n45K4vPrT48AoOZCfg
linkToPdf	http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV3db9MwED-hDgEvfE8UBhgJiadoseMm8WPVrYCoqmrr0N4iO7alSmtakg6U_567JM2YBEJCPMbnRP6688_O3e8A3iuRxCbnMjA89IH0Kg10nFDEMpdcGdxymwu3r7NkPk8vL9Wi8yakWJiWH6K_cCPNaOw1KbjbWn98wxpKzvfkm4WIJqTQ9QNJmWQGcHByNr2Y9eY4Fi3hXigltkCqPXNjKI5vf-H2znQDN38Frc2uM330H9r7GB52kJON2zXyBO644incn-wzvT2Db-OqXq8ptVbOzusCIWG1qtjGsyWW6bzOr1CwqMsSDSUe4SnNj6uYLiyjdJ9Nkgln2bKstzu9bmSmZpqd_1jhkqDQLDbRFfnhszPXxlE8h4vp6XLyKehSMQQ54gcepF6NEhM7nWpLfIbckIOo8spiZ0wUhUIr62JulRDe5SmPfCgswjmpc2tUEh3CoNgU7gUwk1qDm2AcxZHD01KijOTSG-W1NAIHZgjBfhqyvOMpp55cZS3DsshoILN-IIfwoa-_bRk6_ljzaD-rWaepVYbwKaE8Nyr9rRgRoSBKw5EawrtejPND_1V04TbX-ImU7CAePUdDEM0S-EtDsvH842n_9PJfXnoL9xYn02z2ef7lFTygYgqQ5PERDHbltXsNd_Pvu1VVvunU4Sf93wlz
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=Asymmetric+Synthesis+of+Tetracyclic+Pyrroloindolines+and+Constrained+Tryptamines+by+a+Switchable+Cascade+Reaction&rft.jtitle=Angewandte+Chemie&rft.au=deGraaff%2C+Corien&rft.au=Bensch%2C+Lisa&rft.au=Boersma%2C+Sjoerd+J&rft.au=Cioc%2C+Razvan+C&rft.date=2015-11-16&rft.issn=0044-8249&rft.eissn=1521-3757&rft.volume=127&rft.issue=47&rft.spage=14339&rft.epage=14342&rft_id=info:doi/10.1002%2Fange.201507041&rft.externalDBID=NO_FULL_TEXT
thumbnail_l	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0044-8249&client=summon
thumbnail_m	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0044-8249&client=summon
thumbnail_s	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0044-8249&client=summon