title: Total synthesis of the putative structure of the lupin alkaloid plumerinine.
abstract: [reaction: see text]. A stereocontrolled synthesis of quinolizidine 1, the reported structure of plumerinine, has been accomplished in 10 steps from 4-methoxypyridine. The key step is a highly facial selective intramolecular [2 + 2] photocycloaddition of a 2,3-dihydro-4-pyridone. The reported spectral data for plumerinine did not match that of our synthetic 1.
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA. daniels_comins@ncsu.edu
authors.forename: Daniel L
authors.initials: DL
authors.lastname: Comins
authors.forename: Xiaoling
authors.initials: X
authors.lastname: Zheng
authors.forename: R Richard
authors.initials: RR
authors.lastname: Goehring
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis; D001208:Asia; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010946:Plants, Medicinal / Q000737:chemistry*; D011799:Quinazolines / Q000138:chemical synthesis; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000470:Alkaloids; D011799:Quinazolines; C457059:plumerinine