Collect. Czech. Chem. Commun. 1980, 45, 921-926

Synthesis of 14-deoxy-14α-strophanthidol

Pavel Kočovský and Václav Černý

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


A thirteen-step synthesis of 3β,5,19-trihydroxy-5β, 14α-card-20(22)-enolide (I, title compound) from 3β-acetoxy-5-pregnen-20-one (V) is described. A characteristic feature of this approach is the introduction of the 5β-hydroxyl group by hypobromous acid addition to the 5,6-unsaturated-19-acetoxy derivative XV which proceeds with 6(O)π n participation of the acetoxy group (XV(r)XVI(r)XVII).