1508318-92-0Relevant articles and documents
Synthesis of filibuvir. Part I. Diastereoselective preparation of a β-hydroxy alkynyl oxazolidinone and conversion to a 6,6- disubstituted 2H-pyranone
Singer, Robert A.,Ragan, John A.,Bowles, Paul,Chisowa, Esmort,Conway, Brian G.,Cordi, Eric M.,Leeman, Kyle R.,Letendre, Leo J.,Sieser, Janice E.,Sluggett, Gregory W.,Stanchina, Corey L.,Strohmeyer, Holly,Blunt, Jon,Taylor, Stuart,Byrne, Ciaran,Lynch, Denis,Mullane, Sandra,O'Sullivan, Maria M.,Whelan, Marcella
, p. 26 - 35 (2014/05/20)
This is the first in a series of three papers describing the identification and development of a commercial synthesis of filibuvir (1). This contribution describes development of an Evans aldol reaction to control the tertiary alcohol stereocenter, a challenging variant of that strategy in that both reacting partners were nonstandard (acetate enolate and ketone electrophile). A sequence consisting of Sonogashira coupling, acylation and hydrogenation delivered acetate 24, and Dieckmann cyclization provided β-keto lactone 2.
