Total synthesis of the putative structure of the lupin alkaloid plumerinine.
[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.
Comins
Daniel L
DL
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA. daniels_comins@ncsu.edu
Zheng
Xiaoling
X
Goehring
R Richard
RR
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
D000470:Alkaloids; D011799:Quinazolines; C457059:plumerinine