title: Enantioselective syntheses of 2-alkyl- and 2,6-dialkylpiperidine alkaloids: preparations of the hydrochlorides of (-)-coniine, (-)-solenopsin A, and (-)-dihydropinidine.
abstract: [reaction: see text] Sequences of lithiation-substitution, enantioselective hydrogenation, and diastereoselective lithiation-substitution provide efficient highly enantioselective syntheses of 2-substituted and cis and trans 2,6-disubstituted piperidines. The methodology is demonstrated by syntheses of (-)-coniine, (-)-solenopsin A, and (-)-dihydropinidine as their hydrochlorides.
authors.affiliation: Department of Chemistry, University of Illinois at Urbana-Champaign, 61801, USA.
authors.forename: T J
authors.initials: TJ
authors.lastname: Wilkinson
authors.forename: N W
authors.initials: NW
authors.lastname: Stehle
authors.forename: P
authors.initials: P
authors.lastname: Beak
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000700:Analgesics / Q000138:chemical synthesis / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000700:Analgesics; D010880:Piperidines; C409726:dihydropinidine; C002351:Solenopsin A; C007112:coniine