Improved Syntheses of Aromatase Inhibitors and Neuroactive Steroids Efficient Oxidations and Reductions at Key Positions for Bioactivity

摘要

An Henbest reduction, followed by the preparation of a silyl enol ether and oxidation in situ with m-CPBA has led to the neurosteroids 3#alpha#-hydroxy- and 3#alpha#,21-dihydroxy-5#alpha#-pregnanolones. Using testosterone as starting material, a new short synthesis of an aromatase inhibitor, 4-OHA, has been achieved through hydroboration/oxidation followed by a Swern type oxidation and epimerization. Another aromatase inhibitor, androst-4-ene-3,6,17-trione, has been efficiently prepared using PCC on montmorillonite K10, under ultrasonic irradiation.