Stereoselective construction of a steroid 5α,7α-oxymethylene derivative and its use in the synthesis of eplerenone

Bin Zhang; Hongli Chen; Huijin Feng; Yuanchao Li

doi:10.1016/j.steroids.2010.08.009

Stereoselective construction of a steroid 5α,7α-oxymethylene derivative and its use in the synthesis of eplerenone

Steroids. 2011 Jan;76(1-2):56-9. doi: 10.1016/j.steroids.2010.08.009. Epub 2010 Sep 6.

Authors

Bin Zhang¹, Hongli Chen, Huijin Feng, Yuanchao Li

Affiliation

¹ Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, PR China.

PMID: 20826172
DOI: 10.1016/j.steroids.2010.08.009

Abstract

A new and practical method for a stereoselective construction of a steroid 5α,7α-oxymethylene derivative has been developed and successfully applied to the stereoselective synthesis of eplerenone (8). Starting with available 11α-hydroxyl canrenone (1), eplerenone (8) was synthesised in seven steps with a 48% overall yield.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Eplerenone
Molecular Conformation
Spironolactone / analogs & derivatives*
Spironolactone / chemical synthesis
Spironolactone / chemistry
Stereoisomerism

Substances

Spironolactone
Eplerenone