A novel convergent synthesis of the potent antiglaucoma agent travoprost

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 enanti...

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Veröffentlicht in:Tetrahedron 2013-02, Vol.69 (5), p.1634-1648
Hauptverfasser: Dams, Iwona, Chodyński, Michał, Krupa, Małgorzata, Pietraszek, Anita, Zezula, Marta, Cmoch, Piotr, Kosińska, Monika, Kutner, Andrzej
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container_end_page 1648
container_issue 5
container_start_page 1634
container_title Tetrahedron
container_volume 69
creator Dams, Iwona
Chodyński, Michał
Krupa, Małgorzata
Pietraszek, Anita
Zezula, Marta
Cmoch, Piotr
Kosińska, Monika
Kutner, Andrzej
description 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 (7a) yielded travoprost (8a). The main advantages are the preparation of high purity travoprost (8a) and the application of comparatively cheap reagents. The novel convergent strategy allows the synthesis of a whole series of 13,14-en-15-ol PGF2α analogues from a common and structurally advanced prostaglandin intermediate 15. The preparation and identification of two synthetic impurities, 15-epi isomer (8b) of travoprost and a new prostaglandin related ester (5Z)-(+)-18, are also described. [Display omitted]
doi_str_mv 10.1016/j.tet.2012.11.087
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source Elsevier ScienceDirect Journals Complete
subjects Aldehydes
Analogue
Corey lactone
Esters
Hydrolysis
Isomers
Nucleophilic addition
Prostaglandins
Strategy
Synthesis
Tetrahedrons
Travoprost
title A novel convergent synthesis of the potent antiglaucoma agent travoprost
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