Total Synthesis of Vinorine

By:Kang, Shiyuan; Wu, Yinxia; Hu, Min; Ma, Ying; Huang, Xiangdi; Hao, Zhen; Li, Xiujuan; Chen, Wen*; Zhang, Hongbin*

Organic Letters

DOI：10.1021/acs.orglett.3c01041

Published：2023-May-08

Abstract

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.

全文链接：https://pubs.acs.org/doi/10.1021/acs.orglett.3c01041