1510832-83-3Relevant academic research and scientific papers
Synthesis of filibuvir. Part II. Second-generation synthesis of a 6,6-disubstituted 2H-pyranone via dieckmann cyclization of a β-acetoxy ester
Peng, Zhihui,Ragan, John A.,Colon-Cruz, Roberto,Conway, Brian G.,Cordi, Eric M.,Leeman, Kyle,Letendre, Leo J.,Ping, Li-Jen,Sieser, Janice E.,Singer, Robert A.,Sluggett, Gregory W.,Strohmeyer, Holly,Vanderplas, Brian C.,Blunt, Jon,Mawby, Nicola,Meldrum, Kevin,Taylor, Stuart
, p. 36 - 44 (2014/05/20)
This paper describes an improved sequence for the conversion of an oxazolidinone (3) to a β-keto lactone (5). The primary drivers behind this change were the modest and variable yields observed in the intramolecular cyclization to generate the β-keto lactone. Changing the cyclization substrate from oxazolidinone to alkyl ester offered a significantly improved cyclization, as well as improvements in the alkyne hydrogenation. Selection of the optimal substrates for methanolysis and intermediate salt formation are also described.
