Abstract
A convenient synthesis of sidechain-modified phytosterols is achieved via a temporary masking of the stigmasterol 5,6-alkene as an epoxide. Following performance of the desired modification, the alkene is regenerated through a mild deoxygenation. The approach is applied to the syntheses of beta-sitosterol and campesterol acetate, and suggests a facile route to the (Z)-isomers of Delta(22-23) phytosterols.
Copyright 2010 Elsevier Inc. All rights reserved.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Alkenes / chemistry
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Cholesterol / analogs & derivatives
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Cholesterol / chemical synthesis
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Cholesterol / chemistry
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Epoxy Compounds / chemistry
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Phytosterols / chemical synthesis
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Phytosterols / chemistry
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Sitosterols / chemical synthesis*
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Sitosterols / chemistry*
Substances
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Alkenes
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Epoxy Compounds
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Phytosterols
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Sitosterols
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campesterol
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gamma-sitosterol
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Cholesterol