title: IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids: asymmetric synthesis of (+)-luciduline.
abstract: [formula: see text] The first chiral auxiliary mediated asymmetric synthesis of the naturally occurring Lycopodium alkaloid (+)-luciduline has been accomplished. Key steps include an IMDA reaction of a chiral dihydropyridine, a subsequent retro-Mannich ring opening, and a novel cationic reductive cyclization reaction.
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA. daniel_comins@ncsu.edu
authors.forename: D L
authors.initials: DL
authors.lastname: Comins
authors.forename: C A
authors.initials: CA
authors.lastname: Brooks
authors.forename: R S
authors.initials: RS
authors.lastname: al-awar
authors.forename: R R
authors.initials: RR
authors.lastname: Goehring
mesh_terms: D008352:Mannich Bases; D010946:Plants, Medicinal / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D008352:Mannich Bases; D011804:Quinolines; C410447:luciduline