Steroids

Synthesis of polyhydroxysterols (I): synthesis of 24-methylenecholest-4-en-3β, 6β-diol, a cytotoxic natural hydroxylated sterol

JG Cui, LM Zeng, JY Su, WG Lu

Index: Cui, JianGuo; Zeng, LongMei; Su, JingYu; Lu, WeiGang Steroids, 2001 , vol. 66, # 1 p. 33 - 38

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Citation Number: 22

Abstract

Starting from stigmasterol (2), 24-methylenecholest-4-en-3β, 6β-diol (1), a cytotoxic natural dihydroxylated sterol, was synthesized via 10 steps in 20% overall yield. The introduction of a side-chain of sterol was achieved by solid-liquid phase-transfer Wittig reaction using (3- methyl-2-oxo) butyltriphenylarsonium bromide (12) and K2CO3. Construction of the steroidal nucleus was finished by the addition of 3β-acetoxycholest-5, 6-en-24-one (7) with NBA in ...

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