Collect. Czech. Chem. Commun.
1980, 45, 921-926
https://doi.org/10.1135/cccc19800921
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
Abstract
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).
