A reductive-Heck approach to the hydroazulene ring system: a formal synthesis of the englerins.
The reduction of a palladium enolate prior to β-hydride elimination provides a unique reaction for the synthesis of the hydroazulene ring system. When combined with a transannular epoxide rearrangement cascade, the reductive-Heck reaction allows rapid entry to the oxo-bridged guaiane core of the englerins.
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, USA.
Peng
P
Gao
Silas P
SP
Cook
D052176:Azulenes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D052176:Azulenes; D045789:Sesquiterpenes, Guaiane; C534971:englerin A; C551614:englerin B