Synthesis of rac-Lindenene via a thermally induced cyclopropanation reaction.

Fenlon TW, Jones MW, Adlington RM, Lee V

The first synthesis of the sesquiterpene Lindenene is described. A novel non-catalysed intramolecular cyclopropanation reaction between a diazoketone and an unactivated alkene was utilised to construct the relatively labile ketone precursor with complete stereocontrol. This ketone was transformed in three steps into Lindenene.

Keywords:

Alkenes

,

Crystallography, X-Ray

,

Cyclopropanes

,

Furans

,

Ketones

,

Models, Molecular

,

Molecular Conformation

,

Sesquiterpenes

,

Temperature