Sato Keigo, Kogure Noriyuki, Kitajima Mariko, Takayama Hiromitsu
Graduate School of Pharmaceutical Sciences , Chiba University , 1-8-1 Inohana, Chuo-ku , Chiba 260-8675 , Japan.
Org Lett. 2019 May 3;21(9):3342-3345. doi: 10.1021/acs.orglett.9b01084. Epub 2019 Apr 18.
The total syntheses of C-mavacurine-type indole alkaloids, (±)-pleiocarpamine, (±)-normavacurine, and (±)- C-mavacurine, were accomplished. The key step in the syntheses was the cyclization between the metal carbenoid at C and the N position in a Corynanthe-type compound that was equipped with a diazo function. For this cyclization, the N modification of the substrate using an amine-borane complex was indispensable to fix the molecular conformation.
完成了C-马瓦库林型吲哚生物碱（±）-普列奥卡品、（±）-降马瓦库林和（±）-C-马瓦库林的全合成。合成中的关键步骤是在具有重氮功能的柯楠特型化合物中，C位的金属卡宾与N位之间发生环化反应。对于这种环化反应，使用胺-硼烷络合物对底物进行N修饰对于固定分子构象是必不可少的。
