Abstract
AbstractA detailed study of regiospecific silylation, oxidation, and reduction of sterols is reported. The different reactivity of 2α and 3α hydroxy groups is demonstrated on a 2α,3α‐dihydroxy‐5α‐pregnane‐6,20‐dione as a model substrate. A regiospecific silylation of the 2α‐alcohol occurred when silyl chloride was used under mild reaction conditions. The selective oxidation of one of the 2α,3α‐diols by dimethyldioxirane or the Dess–Martin periodinane led to a mixture of α‐hydroxyketones with high prevalence of 3,6,20‐trione over 2,6,20‐trione in the ratio 10:1. A regiospecific reduction of a model substrate by lithium tri‐tert‐butoxyaluminium hydride gives the C6 alcohol.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
