Synthesis of the Potent Antiglaucoma Agent, Travoprost

Autor:	Raymond Mccague, Mark Jackson, Ian C. Lennon, Graham Ruecroft, Nicholas Parkin, Lee T. Boulton, Dean Brick, Martin E. Fox, Darren Rhodes
Rok vydání:	2002
Předmět:	chemistry.chemical_classification Ketone Bicyclic molecule Silylation Organic Chemistry chemistry Yield (chemistry) Wittig reaction medicine Organic chemistry Travoprost Physical and Theoretical Chemistry Enantiomer Lactone medicine.drug
Zdroj:	Organic Process Research & Development. 6:138-145
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op010097p
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::41b64dd498ff6c66a625f10e2c52f4c5 https://doi.org/10.1021/op010097p Zobrazit plný text záznamu