Acid- and base-catalysed reactions of 4β,5β- and 4α,5α-epoxyandrostane-3,17,19-trione

Abstract

The acid- and base-catalysed reactions of 4β, 5β- and 4α, 5α-epoxyandrostane-3,17,19-triones (2) and (7) have been examined to see if epoxide opening in these compounds would result in elimination of the C-10 substituent and the subsequent formation of estrone (25). However, the products obtained indicated that epoxide solvolysis or rearrangement concomitant with epoxide opening is the predominant mode of reaction under the conditions examined.