Uwamori Masahiro, Nakada Masahisa
Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.
Nat Prod Commun. 2013 Jul;8(7):955-9.
The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence, which has been utilized for the total syntheses of nemorosone, garsubellin A, and hyperforin: intramolecular cyclopropanation, formation of a geminal dimethyl group, and regioselective ring opening of cyclopropane. Further elaboration, including chemo- and stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains, was employed to complete the total synthesis ofclusianone.
clusianone的全合成是通过三步序列立体选择性构建双环[3.3.1]壬烷衍生物来完成的，该序列已用于nemorosone、garsubellin A和hyperforin的全合成：分子内环丙烷化、偕二甲基的形成以及环丙烷的区域选择性开环。进一步的修饰，包括化学和立体选择性氢化以生成C7立体中心以及交叉复分解以在侧链中构建异戊烯基，用于完成clusianone的全合成。
