Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Pharmacy, Yunnan University, Kunming, 650091, P. R. China.
Yunnan Provincial Center for Research and Development of Natural Products, Yunnan Characteristic Plant Extraction Laboratory, School of Pharmacy, Yunnan University, Kunming, 650091, P. R. China.
Org Lett. 2023 May 19;25(19):3466-3470. doi: 10.1021/acs.orglett.3c01041. Epub 2023 May 8.
The asymmetric total synthesis of vinorine, a polycyclic and cage-like alkaloid, has been realized in a flexible approach. Key features of the current synthesis include an aza-Achmatowicz rearrangement/Mannich-type cyclization to install the highly functional 9-azabicyclo-[3.3.1]nonane scaffold, a high yield Fischer indole annulation to synthesize the common intermediate for sarpagine-ajamaline type alkaloids, and an Ireland-Claisen rearrangement to construct the C15-C20 bond.
不对称全合成多环笼状生物碱 vinorine 的方法已经实现。目前合成的关键特点包括氮杂-Achmatowicz 重排/Mannich 型环化反应来构建高度功能化的 9-氮杂双环[3.3.1]壬烷骨架，高产率 Fischer 吲哚环合反应来合成 sarpagine-ajamaline 型生物碱的共同中间体，以及 Ireland-Claisen 重排反应来构建 C15-C20 键。
