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Control of the stereochemistry of C14 hydroxyl during the total synthesis of withanolide E and physachenolide C

Yes / The stereochemical outcome of the epoxidation of Δ14–15 cholestanes with mCPBA is controlled by the steric bulk of a C17 substituent. When the C17 is in the β configuration, the epoxide is formed in the α face, whereas if the C17 is trigonal (flat) or the substituent is in the α configuration, the epoxide is formed in the β face. The presence of a hydroxyl substituent at C20 does not influence the stereochemical outcome of the epoxidation. / We thank University of Bradford for a bursary (MA).

Identiferoai:union.ndltd.org:BRADFORD/oai:bradscholars.brad.ac.uk:10454/16691
Date2018 November 1927
CreatorsAnees, Muhammad, Nayak, Sanjit, Afarinkia, Kamyar, Vinader, Victoria
Source SetsBradford Scholars
LanguageEnglish
Detected LanguageEnglish
TypeArticle, Published version
Rights© The Royal Society of Chemistry 2018. Open Access Article. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence, CC-BY

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