ArticleChemistry (Weinheim an der Bergstrasse, Germany)2016
A Synthesis of Exiguaquinol Dessulfate.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Enantioselective Nickel-Catalyzed α-Spirocyclization of Lactones.Organic letters · 2024Article
- Strategies for the Synthesis of the Halenaquinol and Xestoquinol Families of Natural Products.European journal of organic chemistry · 2017Article
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Authors and funding
3 authors.
Funding
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.
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