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Concise synthesis of the Erythrina alkaloid 3-demethoxyerythratidinone via combined rhodium catalysis.

ABSTRACT: The total synthesis of the erythrina alkaloid 3-demethoxyerythratidinone has been achieved via a strategy based on combined rhodium catalysis. The catalytic tandem cyclization effected by the interplay of alkynyl and vinylidene rhodium species allows for efficient access to the A and B rings of the tetracyclic erythrinane skeleton in a single step. The synthesis also features rapid preparation of the requisite precursor for the double ring closure and thus has been completed in only 7 total steps in 41% overall yield.

SUBMITTER: Joo JM

PROVIDER: S-EPMC3042142 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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Concise synthesis of the Erythrina alkaloid 3-demethoxyerythratidinone via combined rhodium catalysis.

Joo Jung Min JM David Ramoncito A RA Yuan Yu Y Lee Chulbom C

Organic letters 20101119 24

The total synthesis of the erythrina alkaloid 3-demethoxyerythratidinone has been achieved via a strategy based on combined rhodium catalysis. The catalytic tandem cyclization effected by the interplay of alkynyl and vinylidene rhodium species allows for efficient access to the A and B rings of the tetracyclic erythrinane skeleton in a single step. The synthesis also features rapid preparation of the requisite precursor for the double ring closure and thus has been completed in only 7 total step ...[more]

PMID: 21090648

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