A Convenient Synthesis of 5,6β-Epoxides of Some Cholesteryl Esters and Δ5-Ketosteroid Derivatives by Catalytic β-Stereoselective Epoxidation

Jean-Claude Marchon; René Ramasseul

doi:10.1055/s-1989-27261

Synthesis 1989; 1989(5): 389-391
DOI: 10.1055/s-1989-27261

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A Convenient Synthesis of 5,6β-Epoxides of Some Cholesteryl Esters and Δ⁵-Ketosteroid Derivatives by Catalytic β-Stereoselective Epoxidation

Jean-Claude Marchon^* , René Ramasseul

^*Laboratoires de Chimie/Chimie de Coordination (UA 1194 du CNRS), Département de Recherche Fondamentale, Centre d'Etudes Nucléaires de Grenoble, F-38041 Grenoble, France

Abstract

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The epoxidation of a series of cholesteryl esters by air in the presence of a catalytic amount of a ruthenium tetramesitylporphyrin complex is described. The preparative procedure, which requires only 4 to 5 mol % of the catalyst, leads to high conversion (76 to 94 %) and very high β-stereoselectivity (> 99 %). Similar results are obtained in the epoxidation of 3β-acetoxyandrost-5-ene-17-one, 3β-acetoxypregn-5-ene-20-one, and 3,3-ethylenedioxycholest-5-ene.

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