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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Vydáno v:	Chemistry : a European journal Ročník 22; číslo 50; s. 17953 - 17957
Hlavní autoři:	Schwarzwalder, Gregg M., Scott, David R., Vanderwal, Christopher D.
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	WEINHEIM Blackwell Publishing Ltd 12.12.2016 Wiley Wiley Subscription Services, Inc
Témata:	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
On-line přístup:	Získat plný text
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Shrnutí:	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.
Bibliografie:	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
ISSN:	0947-6539 1521-3765 1521-3765
DOI:	10.1002/chem.201604506