117711-45-2Relevant articles and documents
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 (1988)
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.
