title: Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived delta-lactam.
abstract: Starting from a common lactam, (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1), or its enantiomer, the enantioselective synthesis of 2-alkylpiperidines and cis- and trans-2,6-dialkylpiperidines is reported. The potential of this approach is illustrated by the synthesis of the piperidine alkaloids (R)-coniine, (2R,6S)-dihydropinidine, (2R,6R)-lupetidine, and (2R,6R)-solenopsin A, the indolizidine alkaloids (5R,8aR)-indolizidine 167B and (3R,5S,8aS)-monomorine I, and the nonnatural base (4R,9aS)-4-methylquinolizidine.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain. amat@farmacia.far.ub.es
authors.forename: Mercedes
authors.initials: M
authors.lastname: Amat
authors.forename: Núria
authors.initials: N
authors.lastname: Llor
authors.forename: José
authors.initials: J
authors.lastname: Hidalgo
authors.forename: Carmen
authors.initials: C
authors.lastname: Escolano
authors.forename: Joan
authors.initials: J
authors.lastname: Bosch
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007212:Indolizines / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010880:Piperidines / Q000138:chemical synthesis*; D011807:Quinolizines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D007202:Indicators and Reagents; D007212:Indolizines; D007769:Lactams; D010880:Piperidines; D011807:Quinolizines; C002351:Solenopsin A