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Control of the stereochemistry of C14 hydroxyl during the total synthesis of withanolide E and physachenolide C
Anees, Muhammad Vinader, Victoria
Anees, Muhammad
Vinader, Victoria
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2018-11
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© The Royal Society of Chemistry 2018. Open Access Article. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence
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16/11/2018
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Abstract
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.
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Anees M, Nayak S, Afarinkia K et al (2018) Control of the stereochemistry of C14 hydroxyl during the total synthesis of withanolide E and physachenolide C. RSC Advances. 8(69): 39691-39695.
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