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.
![cyclohexanepropanoic acid, 2-hydroxy-3-[(2-methoxy-2-oxoethyl)thiol]-4-tetradecylidene-, methyl ester,(1.α,2β,3α,4Z) Structure](https://image.chemsrc.com/caspic/028/106553-89-3.png)