Asymmetric Synthesis of Oxygenated Monoterpenoids of Importance for Bark Beetle Ecology.

ABSTRACT: Herein we report the asymmetric syntheses of a number of oxygenated terpenoids that are of importance in the chemical ecology of bark beetles. These are pinocamphones, isopinocamphones, pinocarvones, and 4-thujanols (= sabinene hydrates). The camphones were synthesized from isopinocampheol, the pinocarvones from β-pinene, and the thujanols from sabinene. The NMR spectroscopic data, specific rotations, and elution orders of their stereoisomers on a chiral GC-phase (β-cyclodextrin) are also reported. This enables facile synthesis of pure compounds for biological activity studies and identification of stereoisomers in mixed natural samples.

SUBMITTER: Ganji S 

PROVIDER: S-EPMC7705961 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature