1. Total synthesis of (+)-nankakurines A and B and (plusmn)-5-epi-nankakurine A
- Author
-
Altman, Ryan A., Nilsson, Bradley L., Overman, Larry E., de Alaniz, Javier Read, Rohde, Jason M., and Taupin, Veronique
- Subjects
Alkaloids -- Chemical properties ,Alkaloids -- Structure ,Club-mosses -- Composition ,Clubmosses -- Composition ,Ring formation (Chemistry) -- Analysis ,Heterocyclic aromatic compounds -- Structure ,Heterocyclic aromatic compounds -- Chemical properties ,Quinoline -- Structure ,Quinoline -- Chemical properties ,Schiff bases -- Chemical properties ,Biological sciences ,Chemistry - Abstract
The first total syntheses of the Lycopodium alkaloids (+)-nankakurine A, (+)-nankakurine B and the originally supported structure of nankakurine A is feature a demanding intramolecular azomethine imine cycloaddition as the key step is reported. The reaction generated the octahydro-3,5-ethanoquinoline moiety and installed the correct relative configuration at the spiropiperidine ring juncture.
- Published
- 2010