Stereoselective Acyclic Synthesis via Allylmetals: An Efficient Synthesis of (±)-4-Methylheptan-3-Ol, an Aggregation Pheromone of the Smaller European Elm Bark Beetle

A highly effiecient, stereoselective synthesis of the insect pheromone (±)-4-methylheptan-3-ol, 4 steps from 1,3-pentadiene with an overall yield of 69.3%, has been achieved using a Lewis-acid catalyzed addition reaction of an allyltin and propanal.