Vasoactive eicosanoids: Synthesis of 12,20-dihydroxyeicosa-5(Z),8(Z),10(E),14(Z)-tetraenoic acid via a novel chiral bis-lactol

The type IIB eicosanoids, 12(R),20- and 12(S),20-dihydroxyeicosatetraenoic acid (DiHETE), were conveniently synthesized utilizing a carbohydrate-derived bis-lactol as a differentiated 4-hydroxyhex-2(E)-enedial chiron. 12(S),20-DiHETE, but not the 12(R)-isomer, induced vasodilation in precontracted canine arteries.