Abstract
Diastereoselective allylation of (R)-2,3-O-cyclohexylideneglyceraldehyde with 3-(bromomethyl)but-3-enoate, followed by reduction with zinc, gave homoallylic alcohol which was subjected to lactonization. Opening of the lactone ring in the latter afforded methyl (3S)-5,5-dimethoxy-3-methylpentanoate with a high yield and enantioselectivity. This compound is a valuable intermediate product in the synthesis of pheromone of the mealworm beetle Tenebrio molitor L., a pest of stored cereals.
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