A novel convergent synthesis of the potent antiglaucoma agent travoprost

…, A Pietraszek, M Zezula, P Cmoch, M Kosińska…

Index: Dams, Iwona; Chodynski, Michal; Krupa, Malgorzata; Pietraszek, Anita; Zezula, Marta; Cmoch, Piotr; Kosinska, Monika; Kutner, Andrzej Tetrahedron, 2013 , vol. 69, # 5 p. 1634 - 1648

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Citation Number: 4

Abstract

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 ...