24-亚甲基-胆甾烷-3β,5α,6β-三醇的合成  

Synthesis of 24-Methylenecholestan-3-β,5α,6β-triol

作　　者：陆伟刚[1] 苏镜娱[1] 曾陇梅[1] 

机构地区：[1]中山大学化学与化学工程学院,广州510275

出　　处：《应用化学》2002年第5期471-473,共3页Chinese Journal of Applied Chemistry

基　　金：国家自然科学基金 (2 993 2 0 3 0 );广东省自然科学基金资助项目 (970 15 4)

摘　　要：Methylenecholestan 3 β,5α,6β triol 1 isolated from the soft coral, Sinularia dissecia has high antifouling property and biodecomposability in natural environment, safe for human bodies. We have synthesized compound 1 in seven steps starting from stigmasterol 2 in overall yield of 31 3%. The side chain of stigmasterol 2 was modified to keto containing structure of compound 3 via hydroxy group and olefin protection, ozonization, wittig reaction and hydrogenation. The A/B ring was modified by oxidation with performic acid to give stereospecific 5 α,6β diol sterol 4. The compound 1 was then obtained by methylenation of cabonyl group at the 24C of 4 through Wittig reaction in a rather strict conditions. The mp, and NMR data of synthesized 1 were in good agreement with that of the natural compound reported by Masaru . This is the first time of the synthesis of 24 methylenecholest 3 β,5α,6β triol 1.Methylenecholestan 3 β,5α,6β triol 1 isolated from the soft coral, Sinularia dissecia has high antifouling property and biodecomposability in natural environment, safe for human bodies. We have synthesized compound 1 in seven steps starting from stigmasterol 2 in overall yield of 31 3%. The side chain of stigmasterol 2 was modified to keto containing structure of compound 3 via hydroxy group and olefin protection, ozonization, wittig reaction and hydrogenation. The A/B ring was modified by oxidation with performic acid to give stereospecific 5 α,6β diol sterol 4. The compound 1 was then obtained by methylenation of cabonyl group at the 24C of 4 through Wittig reaction in a rather strict conditions. The mp, and NMR data of synthesized 1 were in good agreement with that of the natural compound reported by Masaru . This is the first time of the synthesis of 24 methylenecholest 3 β,5α,6β triol 1.

关 键 词：亚甲基-胆甾烷-3β 5α 6β-三醇 合成 豆甾醇 

分 类 号：O629.21[理学—有机化学]