443361-68-0Relevant academic research and scientific papers
An Enantioconvergent Synthesis of (R)-4-Aryloxy-1-butyne-3-ols for Prostanoid Side Chains
Fox, Martin E.,Jackson, Mark,Lennon, Ian C.,McCague, Raymond,Parratt, Julian S.
, p. 50 - 56 (2007/10/03)
The single enantiomer title alcohols, useful as co-side chain precursors for pharmaceutically important prostaglandin analogues were synthesised from the corresponding racemic alcohols by a convenient 4-step sequence. After enzymatic acylation of the alco
Synthesis of the potent antiglaucoma agent, travoprost
Boulton, Lee T.,Brick, Dean,Fox, Martin E.,Jackson, Mark,Lennon, Ian C.,McCague, Raymond,Parkin, Nicholas,Rhodes, Darren,Ruecroft, Graham
, p. 138 - 145 (2013/09/06)
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.
