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Molecules 2017, 22(2), 217;

A Novel Convergent Synthesis of the Potent Antiglaucoma Agent Tafluprost

Chemistry Department, Pharmaceutical Research Institute, Rydygiera 8, 01-793 Warsaw, Poland
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 42/52, 01-224 Warsaw, Poland
Author to whom correspondence should be addressed.
Received: 5 December 2016 / Accepted: 25 January 2017 / Published: 31 January 2017
(This article belongs to the Section Medicinal Chemistry)
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Tafluprost (AFP-168, 5) is a unique 15-deoxy-15,15-difluoro-16-phenoxy prostaglandin F2α (PGF2α) analog used as an efficacious ocular hypotensive agent in the treatment of glaucoma and ocular hypertension, as monotherapy, or as adjunctive therapy to β-blockers. A novel convergent synthesis of 5 was developed employing Julia–Lythgoe olefination of the structurally advanced prostaglandin phenylsulfone 16, also successfully applied for manufacturing of pharmaceutical grade latanoprost (2), travoprost (3) and bimatoprost (4), with an aldehyde ω-chain synthon 17. The use of the same prostaglandin phenylsulfone 16, as a starting material in parallel syntheses of all commercially available antiglaucoma PGF2α analogs 2–5, significantly reduces manufacturing costs resulting from its synthesis on an industrial scale and development of technological documentation. Another key aspect of the route developed is deoxydifluorination of a trans-13,14-en-15-one 30 with Deoxo-Fluor. Subsequent hydrolysis of protecting groups and final esterification of acid 6 yielded tafluprost (5). The main advantages are the preparation of high purity tafluprost (5) and the application of comparatively cheap reagents. The preparation and identification of two other tafluprost acid derivatives, tafluprost methyl ester (32) and tafluprost ethyl amide (33), are also described. View Full-Text
Keywords: tafluprost; prostaglandins; Corey lactone; Julia–Lythgoe olefination; fluorination tafluprost; prostaglandins; Corey lactone; Julia–Lythgoe olefination; fluorination

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Krupa, M.; Chodyński, M.; Ostaszewska, A.; Cmoch, P.; Dams, I. A Novel Convergent Synthesis of the Potent Antiglaucoma Agent Tafluprost. Molecules 2017, 22, 217.

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