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Concise Synthesis of the Erythrina Alkaloid 3-Demethoxyerythratidinone via Combined Rhodium Catalysis

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journal contribution
posted on 17.12.2010, 00:00 by Jung Min Joo, Ramoncito A. David, Yu Yuan, Chulbom Lee
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.