title: Organocatalytic entry into 2,6-disubstituted aza-Achmatowicz piperidinones: application to (-)-sedacryptine and its epimer.
abstract: Enantiomerically pure 2,6-disubstituted piperidinones were synthesized from furfural involving an organocatalyzed Mannich reaction, aza-Achmatowicz reaction, and an N-acyliminium ion-mediated coupling step. This approach was also successfully applied to a total synthesis of (-)-sedacryptine and one of its epimers.
authors.affiliation: Institute for Molecules and Materials, Radboud University Nijmegen , Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
authors.forename: Ferdi
authors.initials: F
authors.lastname: van der Pijl
authors.forename: Robert K
authors.initials: RK
authors.lastname: Harmel
authors.forename: Gaston J J
authors.initials: GJ
authors.lastname: Richelle
authors.forename: Peter
authors.initials: P
authors.lastname: Janssen
authors.forename: Floris L
authors.initials: FL
authors.lastname: van Delft
authors.forename: Floris P J T
authors.initials: FP
authors.lastname: Rutjes
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D017646:Organosilicon Compounds; D010881:Piperidones; C532856:sedacryptine