A Concise Approach to Paxilline Indole Diterpenes

A synthetic approach to paxilline indole diterpenes is described. The route to the penta­cyclic core relies on a new regio­selective alkenyl­ation of ketones and a tandem radical addition–aldol reaction sequence to access vicinal quaternary stereo­centers. Emindole SB, the simplest member of the family, is synthesized in 11 steps from commercially available material to demonstrate the application of this approach.

本研究报道了一种针对帕西林型吲哚二萜（paxilline indole diterpenes）的合成策略。该策略在构建五环核心骨架时，依托于两项关键技术：一种全新的酮区域选择性烯基化反应，以及一套串联自由基加成-羟醛缩合反应序列，用以构筑邻位季碳立体中心。作为该类化合物家族中结构最简单的成员，埃明多SB（Emindole SB）以市售原料为起始物料，经11步反应完成全合成，以此验证了该合成策略的实用性。