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Communication | Regular issue | Vol 6, No. 8, 1977, pp.1097-1100
Published online, 1st January, 1970
DOI: 10.3987/R-1977-08-1097
The Synthesis of 2-Substituted 3-Ketotetrahydrothiophenes Using a Highly Active Dieckmann Catalyst. 11-Desoxy-9-thiaprostaglandin

Wihelmus J. Vloon, Eduard R. de Waard,* and Henderikus O. Huisman

*Laboratory of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129,1018 WS Amsterdam, The Netherlands

Abstract

A highly active form of sodium methoxide permits the Dieckmann cyclisation of diesters of general structure 1 at r.t., without concomitant β-elimination of the sulfide moiety. The conversion of 2- (6’-methoxycarbonylhexyl)-3-ketotetrahydrothiophene (4) to 11-desoxy-9-thiaprostaglandin (8) is described.