ORGN 124 |
| Stephen F. Martin and Shawn M. Amorde. Department of Chemistry & Biochemistry, The University of Texas, 1 University Station A5300, Austin, TX 78712-0165 |
| A new cascade reaction forming aza-[m.n.0]-bicyclic alkaloids from relatively simple aldehydes and amines is reported. This strategy takes advantage of the facile formation and ambident nature of imines. Intramolecular formation of an iminium ion and subsequent alkylation forms four bonds in one step with excellent selectivity. This method is showcased by the total syntheses of (±)-epilupinine and (±)-tashiromine in two steps from known compounds. |
|
New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry |