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: 10.68). 05/2012; 134(22):9126-9. DOI: 10.1021/ja303602f
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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