Efficient access to the core of the Strychnos, Aspidosperma and Iboga alkaloids. A short synthesis of norfluorocurarine.
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.
Martin
David B C
DB
Department of Chemistry, The University of California, Irvine, California 92697-2025, USA.
Vanderwal
Christopher D
CD
D000470:Alkaloids / Q000737:chemistry*; D030009:Aspidosperma / Q000737:chemistry*; D018360:Crystallography, X-Ray; D031451:Strychnos / Q000737:chemistry*; D030014:Tabernaemontana / Q000737:chemistry*; D014403:Tubocurarine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000470:Alkaloids; C541002:norfluorocurarine; D014403:Tubocurarine