Asymmetric total synthesis of antileukemic sesquiterpene (+)-ivalin

The one-pot double alkylation reaction of a chiral α,β-unsaturated imine (6) with isopropenyl Grignard reagent followed by methyl iodide has been shown to proceed highly asymmetrically. Subsequent stereoselective transformation of the derived adduct (10) has culminated in a first asymmetric total synthesis of the optically pure eudesmane sesquiterpene (+)-ivalin (1).