Transformation of steroidal cyclohexadienyl anion without fragmentation: Unexpected synthesis of methylenesteroid

Article abstract of DOI:10.1007/BF02495310

In contrast with androsta-1,4-diene-3α/β,17β-diol, its 3-O-methyl ether is transformed upon C(3)-deprotonation into the corresponding 3-methylene steroid with migration of the O-methyl group on the steroid skeleton (by the scheme of Wittig rearrangement) rather than eliminating the 19-methyl group.