A convenient procedure for the synthesis of 3 beta-hydroxy-6-oxo-5 alpha-steroids. Application to the synthesis of laxogenin

Abstract

A convenient pathway to obtain 3 beta-hydroxy-6-oxo-5 alpha-steroids from 3 beta-acetoxy Delta(5)-steroids is reported

the methodology was applied to the synthesis of laxogenin (7), substance that behaves as a plant growth hormone. This is an alternative way to produce an important functionality found in many examples of naturally occurring steroids. The developed procedure uses inexpensive reagents and can be carried out in four steps. The oxidizing and acidic steps used in this methodology did not affect the labile spiroketal side chain present in diosgenin (16).