Enzymatic synthesis of (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale.

The sex pheromone of Matsucoccus matsumurae Japanese pine bast scale (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one (1) was synthesized with stereocontrol from (2R,4S)-5-acetoxy-2,4-dimethyl-pentanol (3), which in turn was prepared by lipase-catalyzed transesterification of meso-2,4-dimethyl-1,5-propanediol (2).