Studies on Acetylenic Compounds. XV. Synthesis of 16-Ethynylated Steroids.

Abstract

3β, 17β-Diacetoxyandrost-5-en-16-one and 3β-methoxy-17β-acetoxyandrost-5-en-16-one were ethynylated with lithium acetylide. The resulting 16α-ethynyl-16β, 17β-diol afforded 16, 17-acetonide on treating with acetone, one of which was converted into 16α-ethynyl-16β, 17β-dihydroxyandrost-4-en-3-one by Oppenauer oxidation of the corresponding 3-ol and hydrolysis of 16, 17-acetonide.