Instituto de Química de Sao Carlos , Universidade de Sao Paulo , CEP 13560-970 , Sao Carlos , SP , Brazil.
Org Lett. 2019 Aug 2;21(15):6079-6083. doi: 10.1021/acs.orglett.9b02221. Epub 2019 Jul 25.
The short and stereoselective syntheses of diterpenes (±)-brussonol and (±)-komaroviquinone, via a Ni-catalyzed epoxide ring-opening approach in the presence of aryl halides, is described. Key steps involve the effective preparation of a challenging hemiacetal intermediate in a single operation, followed by a highly efficient BF·OEt-catalyzed Friedel-Craft alkylation, to construct the tricyclic skeleton of these diterpenes. The synthetic approach might offer a unified route for the synthesis of several natural products containing icetexane motifs.
本文描述了通过 Ni 催化的环氧化物开环反应，在芳基卤化物存在下，立体选择性地合成二萜类化合物（±）-brussonol 和（±）-komaroviquinone 的简短方法。关键步骤包括在单个操作中有效制备具有挑战性的半缩醛中间体，然后通过高效 BF·OEt 催化的傅克烷基化反应，构建这些二萜的三环骨架。该合成方法可能为含有 icetexane 结构的几种天然产物的合成提供了一种统一途径。
