Hydroxy-steroids. Part XVI. The preparation of 2,3-acetoxy-ketones and 2,3-diols from lupan-3-one

Abstract

Reinvestigation of the reaction between lupan-3-one and lead tetra-acetate has shown the product to be 3-oxolupan-2α-yl acetate. This compound is easily isomerised to 2-oxolupan-3β-yl acetate. Three 2,3-diols were obtained by reducing the acetoxy-ketones; the fourth was prepared by hydrolysing 2α,3α-epoxylupane.

Spectrometric and chemical evidence establishes the configurations of the diols and suggests probable conformations for them.