Article

Total synthesis of Akuammiline alkaloid (-)-vincorine via intramolecular oxidative coupling.

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, China.
Journal of the American Chemical Society (impact factor: 9.91). 05/2012; 134(22):9126-9. DOI:10.1021/ja303602f pp.9126-9
Source: PubMed

ABSTRACT An asymmetric total synthesis of the Akuammiline alkaloid (-)-vincorine (18 steps from 5-methoxytryptamine, 5% overall yield) is described. The key steps include Pd-catalyzed direct C-H functionalization of indole derivatives, organocatalyzed asymmetric Michael addition of aldehydes to alkylidene malonates, and intramolecular oxidative coupling between indole and malonate moieties.

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Keywords

Akuammiline alkaloid
 
indole
 
indole derivatives
 
intramolecular oxidative coupling
 
organocatalyzed asymmetric Michael addition
 
Pd-catalyzed direct C-H functionalization