The 16-(3-trifluoromethyl) phenoxy PGF2α analogue travoprost (8a) has potent topical ocular activity. A novel convergent synthesis of 13, 14-en-15-ol PGF2α analogues was developed employing Julia–Lythgoe olefination of the structurally advanced prostaglandin phenylsulfone (5Z)-(+)-15 with a new enantiomerically pure aldehyde ω-chain synthon (S)- (−)-16a. Subsequent hydrolysis of protecting groups and final esterification of fluprostenol ...