title: Identification and preparation of antiinsectan dienols fromDipterocarpus kerrii tree resins.
abstract: 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.
authors.affiliation: Department of Chemistry, Williams College, 01267-2092, Williamstown, Massachusetts.
authors.forename: D P
authors.initials: DP
authors.lastname: Richardson
authors.forename: A C
authors.initials: AC
authors.lastname: Messer
authors.forename: B A
authors.initials: BA
authors.lastname: Newton
authors.forename: N I
authors.initials: NI
authors.lastname: Lindeman