A Convenient Reduction-Oxidation Procedure for the Selective Epimerization at Sulfur of Highly Functionalized, Optically Active Sulfoxides

L. A. G. M. van den Broek Department of Organic Chemistry, University of Nijmegen, Toernooiveld, 6525, ED, Nijmegen, The Netherlands; Organon International B.V., P.O. Box 20, 5340 BH, Oss, The Netherlands

P. J. A. in't Veld Department of Organic Chemistry, University of Nijmegen, Toernooiveld, 6525, ED, Nijmegen, The Netherlands

J. H. Colstee Department of Organic Chemistry, University of Nijmegen, Toernooiveld, 6525, ED, Nijmegen, The Netherlands

H. C. J. Ottenheijm Department of Organic Chemistry, University of Nijmegen, Toernooiveld, 6525, ED, Nijmegen, The Netherlands; Organon International B.V., P.O. Box 20, 5340 BH, Oss, The Netherlands

Abstract

A convenient method is described for the selective epimerizatin at sulfur of highly functionalized, optically active sulfoxides. The approach followed involves a sulfoxide reduction (with 2-phenylene phosphochloridite) - oxidation (with m-chloroperoxybenzoic acid) - separation of diastereomers sequence of steps. It was applied for the conversion of 3a, 3b and 3c into 2a, 2b and 2C, respectively, key intermediates in the total synthesis of the antitumor antibiotic sparsomycin and derivatives. Overall yields range from 26% to 37%.

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A Convenient Reduction-Oxidation Procedure for the Selective Epimerization at Sulfur of Highly Functionalized, Optically Active Sulfoxides

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A Convenient Reduction-Oxidation Procedure for the Selective Epimerization at Sulfur of Highly Functionalized, Optically Active Sulfoxides

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