Robert J. Cregge

Conformationally restricted leukotriene antagonists. Asymmetric synthesis of some nor-leukotriene D4 analogs

Abstract The enantiomeric pair of conformationally-restricted nor-LTD 4 analogs 10 and 11 have been synthesized stereoselectively from (S)-2-cyclohexen-1-ol.

Conformationally restricted leukotriene antagonists. Asymmetric synthesis of a nor-leokotriene D4 analog. II.

Chiral diol 5 is prepared from cyclohexanone and used in the asymmetric synthesis of nor-leukotriene D4 analog 1.

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

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.