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
Conformationally restricted leukotriene antagonists. Synthesis of chiral 4-hydroxy-4-alkylcyclohexanecarboxylic acids as leukotriene D4 analogs
โ 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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๐ SIMILAR VOLUMES
The enantiomeric pair of conformationally-restricted nor-LTD4 analogs s and 11 have been synthesized stereoselectively from (g)-2-cyclohexen-l-01. Due to our continuing interest in the stereoselective syntheses of conformationallyrestricted LTDl analogsr, we were attracted by recent reports' that 2-
Lewis acid catalyzed allylation of diacetyl-D-xylal 2 is stereoselectlve for ~-C-glycoside 2b, a result used in the syntheses of pyrans 8a, b, from D-xylose. Vhile pursuing approaches to the stereocontrolled syntheses of conformationally-restrlcted LTD 4 receptor antagonists, we became aware of a hi
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