18444-79-6Relevant articles and documents
Structure/odor relationships of (-)- and (+)-β-vetivone, and their demethyl derivatives: Short communication
Spreitzer, Helmut,Piringer, Iris,Holzer, Wolfgang,Widhalm, Michael
, p. 2292 - 2299 (2007/10/03)
(-)-β-Vetivone ((-)-3a), one of the main constituents of vetiver oil, was submitted to a structure/odor relationship study. The influence of the Me groups at the cyclohexenone ring and of the configuration on the odor was examined. Detailed 1H- and 13C-NMR-spectroscopic data were collected, and the absolute configurations were determined by CD methods.
An Asymmetric Total Synthesis of Fragrant Spirodecane Sesquiterpene (-)-β-Vetivone via an Enantiomerically Pure Vinylic Sulfoxide
Posner, Gary H.,Hamil, Terence G.
, p. 6031 - 6035 (2007/10/02)
A nonenzymatic asymmetric synthesis of (R)-(+)-3-methylpentanolide 4 in 93percent enantiomeric purity has been achieved involving novel methyltitanium triisopropoxide conjugate methyl addition to enantiomerically pure p-anisylpentenolide sulfoxide (S)-(+)-5b.One step, five-membered ring spiroannulation then formed a quaternary carbon center in a stereospecific fashion to give spiroheterocycle (-)-3.Spiroheterocycle (-)-3 was converted directly into natural spirocarbocycle (-)-β-vetivone, 1, constituting the third asymmetric total synthesis of this commercially valuable fragrant sesquiterpene.