Steroids. Part XV. Rearrangements of 9- and 10-hydroxy-5β-methyl-19-nor-steroids

Abstract

The backbone rearrangement of 10β-hydroxy-5βmethyl-19-nor-steroids is susceptible to changes in substituents at C(6) and to changes in the reaction medium. 9α-Hydroxy-5β-methyl-19-nor- and 10α-hydroxy-5β-methyl-19-nor-9β-steroids are simply dehydrated. The mechanisms of the backbone and the related Westphalen rearrangements are discussed. An anthrasteroid rearrangement of a 10β-hydroxy-5β-methyl-6-oxo-19-nor-steroid is reported.