title: Modified Julia Olefination on Anhydrides: Extension and Limitations. Application to the Synthesis of Maculalactone B.
abstract: The preparation of exo-enol esters from cyclic anhydrides is reported using a modified Julia olefination. The reaction is highly stereoselective. The Smiles rearrangement can be performed in a one-pot process, giving a straightforward access to exo-enol lactones. Furthermore, the reaction was extended to semistabilized sulfones, and this methodology was applied to the synthesis of maculalactone B.
authors.affiliation: Université de Lyon, ICBMS, UMR 5246 - CNRS, Bat. 308 - Curien (CPE Lyon), Université Claude Bernard Lyon 1 , 43 Bd du 11 Novembre 1918, F-69622 Villeurbanne, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Dussart
authors.affiliation: Université de Lyon, ICBMS, UMR 5246 - CNRS, Bat. 308 - Curien (CPE Lyon), Université Claude Bernard Lyon 1 , 43 Bd du 11 Novembre 1918, F-69622 Villeurbanne, France.
authors.forename: Huu Vinh
authors.initials: HV
authors.lastname: Trinh
authors.affiliation: Université de Lyon, ICBMS, UMR 5246 - CNRS, Bat. 308 - Curien (CPE Lyon), Université Claude Bernard Lyon 1 , 43 Bd du 11 Novembre 1918, F-69622 Villeurbanne, France.
authors.forename: David
authors.initials: D
authors.lastname: Gueyrard