Control of the Stereochemistry of C14 Hydroxyl During the Total Synthesis of Withanolide E and Physachenolide C

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 13

PMID 35558026

Authors

M Anees

S Nayak

K Afarinkia

V Vinader

Affiliations

Soon will be listed here.

Abstract

The stereochemical outcome of the epoxidation of Δ 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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