Synthetic research on hepoxilins. 7.* Divergent total synthesis of hepoxilins and related eicosanoids

Article abstract of DOI:10.1007/BF02503497

A new synthetic strategy for hydroxy-epoxy eicosanoids formed through the lipoxygenase pathway is developed. It makes use of a single synthon of the central functionalized fragment of the target molecules, namely racemic (E)-CICH₂C≡CCHOHCH=CHCH₂OBz. Elongation of the carbon chain of the synthon by successive condensations at both ends altenatively with hept-1-yne and hex-5-ynoic acid followed by enantioselective double bond epoxidation and partial hydrogenation of the triple bonds resulted in the syntheses of hepoxilins B₃, their potential 8-lipoxygenase analogs, or their enantiomers, depending on the sequence of carbon chain elongations and the chirality of the epoxidation controller used.