Issue 14, 1983

A new synthesis of a steroid side chain via stereocontrolled protonation: synthesis of (–)-desmosterol

Abstract

Protonation of the lactone enolate (9), obtained from the 20-cyano-steroid (3) and (R)-benzyl 2,3-epoxypropyl ether (6), with saturated aqueous sodium sulphate proceeds in a highly steroselective manner from the less hindered side to give the (20R)-lactone (10) which can be converted into the (20R)-steroid, desmosterol (17).

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1983, 760-761

A new synthesis of a steroid side chain via stereocontrolled protonation: synthesis of (–)-desmosterol

S. Takano, S. Yamada, H. Numata and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1983, 760 DOI: 10.1039/C39830000760

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