SYNTHETIC RESEARCH ON HEPOXILINS - 7 - DIVERGENT TOTAL SYNTHESIS OF HEPOXILINS AND RELATED EICOSANOIDS

A new synthetic strategy for hydroxy-epoxy eicosanoids formed through the lipoxygenase pathway is developed. It makes use of a single syntho n of the central functionalized fragment of the target molecules, name ly racemic (E)-ClCH2C=CCHOHCH=CHCH(2)OBz. Elongation of the carbon cha in of the synthon by successive condensations at both ends alternative ly with hept-1-yne and hex-5-ynoic acid followed by enantioselective d ouble bond epoxidation and partial hydrogenation of the triple bonds r esulted in the syntheses of hepoxilins B-3, their potential 8-lipoxyge nase analogs, or their enantiomers, depending on the sequence of carbo n chain elongations and the chirality of the epoxidation controller us ed.