Synthesis of the potent antiglaucoma agent, travoprost

被引：34

作者：

Boulton, LT ^{[1
]}

Brick, D ^{[1
]}

Fox, ME ^{[1
]}

Jackson, M ^{[1
]}

Lennon, IC ^{[1
]}

McCague, R ^{[1
]}

Parkin, N ^{[1
]}

Rhodes, D ^{[1
]}

Ruecroft, G ^{[1
]}

机构：

[1] Chirotech Technol Ltd, Cambridge CB4 0WG, England

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2002年 / 6卷 / 02期

关键词：

D O I：

10.1021/op010097p

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A commercial synthesis of the antiglaucoma agent, travoprost 2, is described. A total of 22 synthetic steps are required to provide the single enantiomer prostanoid, with the longest linear sequence being 16 steps from 3-hydroxybenzotrifluoride. The route is based upon a cuprate-mediated coupling of the single enantiomer vinyl iodide 13 and the tricyclic ketone 5, of high stereochemical purity, to yield the single isomer bicyclic ketone 15. A Baeyer-Villiger oxidation provides the lactone 16 as a crystalline solid, thus limiting the need for chromatographic purification. DIBAL-H reduction, Wittig reaction, esterification, and silyl group deprotection complete the synthesis of travoprost.

引用

页码：138 / 145

页数：8

共 29 条

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[Anonymous], 1983, Jpn. Kokai Tokkyo Koho, Jpn. Patent, Patent No. [58041836, 74856]

[2]

Bowler J., 1982, Patent No. [US4321275A, 4321275]

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