Tandem cationic aza-cope rearrangement-Mannich cyclization approach to the core structure of FR901483 via a Bridgehead iminium ion.
[reaction in text] An approach to the potent immunosuppressant FR901483 is described. This route utilizes a tandem cationic aza-Cope rearrangement-Mannich cyclization to generate the core structure of this compound. In addition, this is the first demonstration of this tandem reaction passing through a bridgehead iminium ion.
Brummond
K M
KM
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, USA. kbrummon@wvu.edu
Lu
J
J
D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry; D007166:Immunosuppressive Agents / Q000737:chemistry*; D007477:Ions / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D003512:Cyclohexanones; C098358:FR 901483; D007166:Immunosuppressive Agents; D007477:Ions; D009943:Organophosphorus Compounds; C036468:cyclohexanone