Total synthesis of 5(S),20- and 15(S),20-dihydroxyeicosatetraenoic acid and 5(S),6(R)-epoxy-20-hydroxy- and 14(R),15(S)-epoxy-20-hydroxyeicosatreinoic acid
Abstract
Aldehyde (1), derived from dimethyl L-malate, was exploited in a stereocontrolled total synthesis of the ω-hydroxylated eicosanoid metabolites 5(S),20- and 15(S),20-dihydroxyeicosatetraenoic acid as well as 5(S),6(R)-epoxy-20-hydroxy- and 14(R),15(S)-epoxy-20-hydroxyeicosatrienoic acid.