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Citation: LU Wei-Gang, SU Jing-Yu, ZENG Long-Mei. Synthesis of 24-Methylenecholestan-3β,5α,6β-triol[J]. Chinese Journal of Applied Chemistry, ;2002, 19(5): 471-473. shu

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

1.
School of Chemistry and Chemical Engineering, Sun Yat Sen University, Guangzhou 510275

Corresponding author: ZENG Long-Mei,
Received Date: 1 September 2001
Available Online: 11 January 2002
Fund Project: 国家自然科学基金(29932030) (29932030)广东省自然科学基金资助项目(970154) (970154)

24-Methylenecholestan-3U,5T,6U-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 5T,6U-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, [T] and NMR data of synthesized 1 were in good agreement with that of the natural compound reported by Masaru^[4]. This is the first time of the synthesis of 24-methylenecholest 3U,5T,6U-triol 1.
- methylenecholestan-3U,5T,6U-triol,
- synthesis,
- stigmasterol
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