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Nine-step enantioselective total synthesis of (-)-vincorine.

ABSTRACT: A concise and highly enantioselective total synthesis of the akuammiline alkaloid (-)-vincorine has been accomplished. A key element of the synthesis is a stereoselective organocatalytic Diels-Alder, iminium cyclization cascade sequence, which serves to construct the tetracyclic alkaloid core architecture in one step from simple achiral precursors. The challenging seven-membered azepanyl ring system is installed by way of a single electron-mediated cyclization event initiated from an acyl telluride precursor. The total synthesis of (-)-vincorine is achieved in nine steps and 9% overall yield from commercially available starting materials.

SUBMITTER: Horning BD

PROVIDER: S-EPMC3667606 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

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Nine-step enantioselective total synthesis of (-)-vincorine.

Horning Benjamin D BD MacMillan David W C DW

Journal of the American Chemical Society 20130419 17

A concise and highly enantioselective total synthesis of the akuammiline alkaloid (-)-vincorine has been accomplished. A key element of the synthesis is a stereoselective organocatalytic Diels-Alder, iminium cyclization cascade sequence, which serves to construct the tetracyclic alkaloid core architecture in one step from simple achiral precursors. The challenging seven-membered azepanyl ring system is installed by way of a single electron-mediated cyclization event initiated from an acyl tellur ...[more]

PMID: 23586842

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