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Conformationally restricted leukotriene antagonists. Stereoselective synthesis of some leukotriene D4 analogs

โœ Scribed by Jeffrey S. Sabol; Philip M. Weintraub; Thomas H. Gieske; Robert J. Cregge

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
385 KB
Volume
46
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

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, regiospecific epoxide ring opening with methyl mercaptoacetate to diesters 8 and 12, and saponification to 2a, b.

The peptidoleukotrienes LTC4, LTD4 and LTE4 (1) the arachidonic acid metabolites collectively known as slow-reacting substance of anaphylaxis.

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