Enzymatic Desymmetrization of meso-2,6-Dimethyl-1,7-heptanediol. Enantioselective Formal Synthesis of the Vitamin E Side Chain and the Insect Pheromone Tribolure

The chiral syn -1,5-dimethylalkyl subunit is found in many natural products with significant biological activities. Enzymatic esterification of meso -2,6-dimethyl-1,7-heptanediol with isopropenyl acetate in the presence of Pseudomonas cepacia lipase in organic medium provided the chiral nonracemic monoester in high enantiomeric excess (ee = 95%). This chiral building block was used in the formal syntheses of vitamin E side chain and the insect pheromone tribolure.