Identification and preparation of antiinsectan dienols fromDipterocarpus kerrii tree resins

Originally isolated fromDipterocarpus kerrii, the two previously uncharacterized sesquiterpenes,1 and20, were synthesized from α-gurjunene. A novel process involvingm-chloroperoxybenzoic acid oxidation ofα-gurjunene produced20 in one step. Spectroscopic studies determined that the diene moiety in20 is nonconjugated and also found the C-4 tertiary alcohol center to have theα-configuration, while the other stereocenters have configurations matching the corresponding centers inα-gurjunene. Bioassays with termites demonstrated that20 was more toxic than1, resulting in a 50% mortality in seven days when offered toNeotermes ?dalbergiae on filter papers. The chemicals appear to result from biotransformation ofα-gurjunene. In view of its similarity to the known sesquiterpeneγ-gurjunene, we suggest that20 be referred to asγ-gurjunenol.