16α-Hydroxymethyl-5α-androstane-3β,17β-diol and 16β-hydroxymethyl-5α-androstane-3β,17β-diol, were obtained from reduction of 16-acetoxymethylene-5α-androstan-17-one. The corresponding 16α,17α- and 16β,17α-hydroxymethyl isomers were obtained by neighboring group participation of the 16- and 17-acetates, respectively. The reactions involving carbocation formation also led to ring D rearrangement products.
- Neighboring group participation
- Wagner-Meerwein rearrangement
ASJC Scopus subject areas
- Molecular Biology
- Clinical Biochemistry
- Organic Chemistry