A concise synthesis of β-sitosterol and other phytosterols

Authors

Jiliang Hang, University of Nebraska–LincolnFollow
Patrick Dussault, University of Nebraska-LincolnFollow

Document Type

Article

Date of this Version

12-2010

Comments

Published in Steroids 75:12 (December 2010), pp. 879–883; doi: 10.1016/j.steroids.2010.05.016 Copyright © 2010 Elsevier Inc. Used by permission

Abstract

A convenient synthesis of sidechain-modified phytosterols is achieved via a temporary masking of the stigmasterol 5,6-alkene as an epoxide. Following performance of the desired modification, the alkene is regenerated through a mild deoxygenation. The approach is applied to the syntheses of β-sitosterol and campesterol acetate, and suggests a facile route to the (Z)-isomers of Δ^22–23 phytosterols.

Includes Supplementary Data.