An unusualD-homo-rearrangement of a 14α,17β,20α-trihydroxywithanolide. Crystal and molecular structure of 5-hydroxy-14α,17α-epoxy-17β-methyl-5β-D-homoandrostan-1,17a-dione

Abstract

Cleavage of the C(20)–C(22) bond in a derivative of withanolide E (1), followed by oxidation, afforded the D-homoandrostane derivative (2), whose structure was determined by X-ray analysis; the mechanistic aspects of this unusual rearrangement are discussed.