Total synthesis of leukotriene E4, a member of the SRS-A family

Article abstract of DOI:10.1021/ja00349a052

Leukotriene E₄ and two analogues homo-LTE₄ and nor-LTE₄ have been prepared via the intermediate epoxides. The epoxides were formed by the coupling of a polyenyne sulfonium salt with the required aldehyde-ester in a biphasic reaction system employing aqueous sodium hydroxide as the base for the generation of the ylide. Reduction of the acetylene bonds yielded the desired polyene epoxides which on treatment with L-cysteine methyl ester gave a 1:1 mixture of diastereomers from which the 5S,6R isomers were separated.