Bakers' yeast mediated preparation of (S)-3-(2-furyl)-2-methylpropan-1-ol, a bifunctional chiral C5 isoprenoid synthon: synthesis of (4R,8R)-4,8-dimethyldecanal, a pheromone of Tribolium castaneum

Abstract

Bakers' yeast reduction of the α,β-unsaturated aldehyde (4), leads to the preparation of the bifunctional chiral synthon (2) in enantiomerically pure form and high chemical yield. The mechanism of the reduction is discussed. The usefulness of the chiral synthon (2) is exemplified by its transformation into optically pure (S)-3-methyl-γ-butyrolactone (8) and by the synthesis of (4R,8R)-4,8-dimethyldecanal, the pheromone of Tribolium castaneum.