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...

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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
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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
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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
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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...
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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
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