Steroids

Synthesis of polyhydroxysterols (V): efficient and stereospecific synthesis of 24-methylene-cholest-5-ene-3β, 7α-diol and its C-7 epimer

W Lu, C Zhang, L Zeng, J Su

Index: Lu, Weigang; Zhang, Cuixian; Zeng, Longmei; Su, Jingyu Steroids, 2004 , vol. 69, # 13-14 p. 803 - 808

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Citation Number: 19

Abstract

This paper describes the efficient and stereospecific synthesis of cytotoxic dihydroxylated sterols, 24-methylene-cholest-5-ene-3β, 7α-diol 1, and its C-7 epimer, 24-methylene-cholest- 5-ene-3β, 7β-diol 2. The crux of the synthesis is that the selective allylic oxidation of 24- methylene-cholesteryl acetate proceeds to 24-methylene-7-keto-cholesteryl acetate without extensive byproduct formation from reaction at the Δ24 (28) double bond. This ...