Tetrahedron

Conformationally restricted leukotriene antagonists. Stereoselective synthesis of some leukotriene D 4 analogs

JS Sabol, PM Weintraub, TH Gieske, RJ Cregge

Index: Sabol, Jeffrey S.; Weintraub, Philip M.; Gieske, Thomas H.; Cregge, Robert J. Tetrahedron, 1990 ,  vol. 46,  # 12  p. 4155 - 4160

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Citation Number: 4

Abstract

The stereocontrolled synthesis of conformationally restricted LTD4 analogs 2a, b is described. Epoxidation of enone 4 affords a 2.4: 1 mixture of trans-epoxide 5 and cis- epoxide 9. Stereocontrolled elaboration of each epoxide to final product involves stereoselective Wittig olefination to Z-olefins 6 and 10, regiospecifie epoxide ring opening with methyl mercaptoacetate to diesters 8 and 12, and saponification to 2a, b.