A concise total asymmetric synthesis of the tetrahydronaphthyridine alkaloid (-)-normalindine has been accomplished via the addition of a laterally metalated 4-methyl-3-cyanopyridine to a sulfinimine (N-sulfinyl imine) as the key step.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2543119PMC
http://dx.doi.org/10.1021/jo061443+DOI Listing

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