Synthesis of Filibuvir. Part II. Second-Generation Synthesis of a 6,6-Disubstituted 2H-Pyranone via Dieckmann Cyclization of a β-Acetoxy Ester

Autor:	Stuart Taylor, Gregory W. Sluggett, Brian G. Conway, Leo Joseph Letendre, Robert A. Singer, Nicola Mawby, Kevin Meldrum, Jon Blunt, Zhihui Peng, Kyle R. Leeman, John A. Ragan, Holly Strohmeyer, Eric M. Cordi, Li-Jen Ping, Janice E. Sieser, Roberto Colon-Cruz, Brian C. Vanderplas
Rok vydání:	2013
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Filibuvir Stereochemistry Organic Chemistry Intramolecular cyclization Alkyne Substrate (chemistry) Physical and Theoretical Chemistry Salt formation Alkyl Lactone
Zdroj:	Organic Process Research & Development. 18:36-44
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op400236r
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::249802ea1a0efa9c951d4e02f1bee3a6 https://doi.org/10.1021/op400236r Zobrazit plný text záznamu