From Enynyl Esters to Functionalized Polycyclic Derivatives via Cycloisomerization and Post-Functionalization

Simon Guelen (1) , Max Blazejak (1) , Virginie Mouriès-Mansuy (1) , Louis Fensterbank (1)

1 IPCM - Institut Parisien de Chimie Moléculaire

The post-functionalization of ketone products originating from the PtCl2-catalyzed cycloisomerization of enynyl esters is described. Postfunctionalization has been accomplished via diastereoselective alkylation, regioselective cyclopropane opening and regioselective Baeyer Villiger and Beckmann rearrangements to provide functionalized polycycles.

Mots clés: cycloisomerization; platinum; enynyl ester; polycyclic ketone; Baeyer-Villiger; Beckmann rearrangement; lactones; lactams

Domaines: Chimie organique

Simon Guelen, Max Blazejak, Virginie Mouriès-Mansuy, Louis Fensterbank. From Enynyl Esters to Functionalized Polycyclic Derivatives via Cycloisomerization and Post-Functionalization. Synthesis: Journal of Synthetic Organic Chemistry, 2016, 48 (19), pp.3199 - 3206. ⟨10.1055/s-0035-1561488⟩. ⟨hal-01400636⟩