Asymmetric Synthesis of Oxygenated Monoterpenoids of Importance for Bark Beetle Ecology,Journal of Natural Products

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Asymmetric Synthesis of Oxygenated Monoterpenoids of Importance for Bark Beetle Ecology
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-11-10 , DOI: 10.1021/acs.jnatprod.0c00669
Suresh Ganji ₁ , Fredric G Svensson ₁ , C Rikard Unelius ₁

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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.

中文翻译：

对树皮甲虫生态学具有重要意义的含氧单萜的不对称合成

在此，我们报告了许多含氧萜类化合物的不对称合成，这些萜类化合物在树皮甲虫的化学生态学中具有重要意义。它们是松蒎酮、异松蒎酮、松香芹酮和 4-侧柏烯醇（= 桧烯水合物）。樟脑由异松蒎酚合成，松香芹酮由β-蒎烯合成，侧柏酚由桧烯合成。还报道了其立体异构体在手性 GC 相（β-环糊精）上的 NMR 光谱数据、比旋光度和洗脱顺序。这使得能够轻松合成纯化合物，用于生物活性研究和混合天然样品中立体异构体的鉴定。

更新日期：2020-11-25

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