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-
Conformationally restricted leukotriene antagonists. Asymmetric synthesis of a nor-leokotriene D4 analog. II.
โ Scribed by Jeffrey S Sabol; Robert J Cregge
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 229 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
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
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