Journal
ORGANIC LETTERS
Volume 12, Issue 24, Pages 5704-5707Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol102535u
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Funding
- NSF [CHE 518559]
- NIH [R01GM073065]
- Bristol-Myers Squibb
- National Research Foundation of Korea (NRF)
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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 allrynyl 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.
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