Biomimetic Total Syntheses of Ergot Alkaloids via Decarboxylative Giese Coupling
Yuhua Ge, Hang Wang, Hua-Nan Wang, YU Shu-sheng, Yang Rui, Xingyue Chen, Qin Zhao, Gang Chen
Abstract
Biomimetic total syntheses of Festuclavine and Pyroclavine were achieved by a sequential radical coupling. The key steps include intramolecular decarboxylative Giese reaction to form the central C ring and 4-nitrobenzenesulfonyl (Ns)-directed indole C4–H olefination to introduce the indole C4 component. In addition, D-ring formation was completed by decarboxylative alkenylation and intramolecular SN2 reaction.
Topics & Concepts
ChemistryIndole testIntramolecular forceSN2 reactionRing (chemistry)StereochemistryTotal synthesisCombinatorial chemistryCoupling reactionOrganic chemistryCatalysisChemical synthesis and alkaloidsAdvanced Synthetic Organic ChemistryPlant and fungal interactions