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Paper

Org. Biomol. Chem., 2009, 7, 5067 - 5073, DOI: 10.1039/b915796d

Total synthesis of (5R,6R,8R,9S)-(-)-5,9Z-indolizidine 221T using sulfinimine-derived N-sulfinyl -amino ketones

Franklin A. Davis, Minsoo Song, Hui Qiu and Jing Chai

The first total asymmetric synthesis of the poison frog alkaloid (-)-221T, a 5,6,8-trisubstituted indolizidine is described. The key core piperidine ring was constructed via an acid catalyzed intramolecular cascade Mannich cyclization reaction of a N-sulfinyl syn--methyl -amino ketone and crotonaldehyde. The -amino ketone was prepared via the reaction of prochiral lithium Weinreb amide enolate with an enantiopure N-2,4,6-triisopropylphenylsulfinyl imine.

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