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Conformationally restricted leukotriene antagonists. Synthesis of chiral 4-hydroxy-4-alkylcyclohexanecarboxylic acids as leukotriene D4 analogs

โœ Scribed by Cregge, Robert J.; Lentz, Nelsen L.; Sabol, Jeffrey S.


Book ID
126245120
Publisher
American Chemical Society
Year
1991
Tongue
English
Weight
783 KB
Volume
56
Category
Article
ISSN
0022-3263

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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

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Synthetic Approaches to 2-(4-Hydroxy-7-chromanyl)benzoic Acids as Antagonists of Leukotriene B 4 . -Two different ways to prepare desired title compounds (VII) and (XI) are used. The first includes seven steps, uses organostannane biaryl coupling and non-stereoselective reduction, which limits this