Catalysis-based enantioselective total synthesis of the macrocyclic spermidine alkaloid isooncinotine.
A concise and efficient total synthesis of the spermidine alkaloid (-)-isooncinotine (1) incorporating a 22-membered lactam ring is outlined. The approach is largely catalysis-based, involving a selective iron-catalyzed alkyl-aryl cross-coupling reaction of a difunctionalized pyridine substrate, a heterogeneous asymmetric hydrogenation step to set the chiral center of the target, and a highly integrated ring-closing metathesis/hydrogenation sequence to forge the saturated macrocyclic edifice in a single operation.
Scheiper
Bodo
B
Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany.
Glorius
Frank
F
Leitner
Andreas
A
Fürstner
Alois
A
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D015394:Molecular Structure; D013095:Spermidine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; C014061:isooncinotine; D013095:Spermidine