Total Synthesis of Vilmoraconitine
Jiujian Ji, Jiajun Chen, Sixun Qin, Wanye Li, Zhao Jun, Guozhao Li, Hao Song, Xiaoyu Liu, Yong Qin
Abstract
-diterpenoid alkaloids, which architecturally features an unprecedented heptacyclic core possessing a rigid cyclopropane unit. Here, we report the first total synthesis of vilmoraconitine relying on strategic use of efficient ring-forming reactions. Key steps include an oxidative dearomatization-induced Diels-Alder cycloaddition, a hydrodealkenylative fragmentation/Mannich sequence, and an intramolecular Diels-Alder cycloaddition.
Topics & Concepts
ChemistryCycloadditionIntramolecular forceCyclopropaneTotal synthesisStereochemistryFragmentation (computing)Ring (chemistry)Organic chemistryCatalysisComputer scienceOperating systemPlant-based Medicinal ResearchBioactive Natural Diterpenoids ResearchAlkaloids: synthesis and pharmacology