Total synthesis of (-)-normalindine via the addition of metallated 4-methyl-3-cyanopyridine to an entantiopure sulfinimine

ORGN 99

Franklin A. Davis, Jeffrey Y. Melamed, and Steve S. Sharik. Department of Chemistry, Temple University, 13th and Norris streets, Philadelphia, PA 19122
Enantiopure sulfinimines are excellent building blocks for the asymmetric synthesis of tetrahydroisoquinolines. Addition of the laterally metallated 4-methyl-3-cyanopyridine to sulfinimine 1 affords 2 in excellent yield and good de. Limitations of the Pictet-Spengler and Bishler-Napieralski procedures, in which electron rich rings are often necessary for ring closure are overcome using this procedure. The application of this methodology towards the total synthesis of the alkaloid (-)-normalindine will be presented.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004