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

Description

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).

Links & Downloads

1. 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.
2. http://hdl.handle.net/10454/16691
3. https://doi.org/10.1039/c8ra08540d

Tags

Stereochemistry

Epoxidation

C14 hydroxyl

Additional Fields

Identifer	oai:union.ndltd.org:BRADFORD/oai:bradscholars.brad.ac.uk:10454/16691
Date	2018 November 1927
Creators	Anees, Muhammad, Nayak, Sanjit, Afarinkia, Kamyar, Vinader, Victoria
Source Sets	Bradford Scholars
Language	English
Detected Language	English
Type	Article, 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