Chemistry Letters

Stereocontrolled synthesis of (22R)-22-hydroxycholesterol guided by. ALPHA.-silyl radical stabilization.

M Koreeda, IA George

Index: Koreeda, Masato; George, Irene A. Chemistry Letters, 1990 , p. 83 - 86

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Citation Number: 11

Abstract

The synthesis of (22R)-22-hydroxycholesterol, featuring formation of three contiguous chiral centers (C-17, 20, and 22) in a single step by the use of a 6-endo α-silyl radical-mediated cyclization is presented. Additionally, an interesting protiodesilylation used to activate a cyclic siloxane towards C–Si bond oxidation, and a modified, bulky aryl thionocaronate reagent for regioselective diol-monodeoxygenation are described.