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Efficient Access to the Core of the Strychnos , Aspidosperma and Iboga Alkaloids. A Short Synthesis of Norfluorocurarine

2009; American Chemical Society; Volume: 131; Issue: 10 Linguagem: Inglês

10.1021/ja900640v

1943-2984

David B. C. Martin, Christopher D. Vanderwal,

Chemical synthesis and alkaloids

An efficient anionic bicyclization of tryptamine-derived Zincke aldehydes forms the basis for a three-step route to the tetracyclic ABCE core of many Strychnos, Aspidosperma, and Iboga alkaloids. This powerful reaction is showcased in a five-step synthesis of the Strychnos alkaloid norfluorocurarine from tryptamine and pyridine.