Synthesis of Exdysone.I.A Novel Synthesis of 2β, 3β-Dihydroxy Steroids

Abstract

A novel synthesis of 2[beta],3[beta]-dihydroxy steroids from 3-oxo compounds in 5a-series was developed. Autoxidation of 3-oxo compound afforded an enol mixture of 2,3-dioxo compounds, which on reduction with sodium borohydride yielded 2[beta],30-dihydroxy steroid. It was found that 2[beta],3[beta]-dihydroxy steroid was obtained with high stereospecificity by the reduction of 2-hydroxy-l-en-3-oxo steroid.