Abstract: (2S,3R) Sitophilate, the major component of the aggregation pheromone of the granary weevil (Sitophilus granarius) was stereoselectively synthesized by a four-step sequence, using N-bornane-2,10-sultam as a chiral auxiliary. The key step was the asymmetric syn aldolization of N-propionyl bornane-2,10-sultam with propylaldehyde. The enantiometric excess of (2S,3R) sitophilate was about 95%ee.

Key words: (2S,3R) sitophilate, synthesis, asymmetric syn-aldolization, N-bornane-sultam