title: Total synthesis of the tetracyclic lupin alkaloid (+)-allomatrine.
abstract: (+)-Allomatrine (1) has been synthesized using an imino-aldol reaction and N-acyliminium cyclization as key steps. Strategically, use of the tert-butylsulfinimine derivative of (E)-4-(trimethylsilyl)but-2-enal enabled the staged formation of three C-C bonds, a C-N bond, and the four stereogenic centers within the target.
authors: Department of Chemistry, The University of Southampton, Highfield, Southampton SO17 1BJ, UK.
authors: Samuel V
authors: SV
authors: Watkin
authors: Nicholas P
authors: NP
authors: Camp
authors: Richard C D
authors: RC
authors: Brown
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D008968:Molecular Conformation; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D029909:Sophora / Q000737:chemistry; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry; D000093842:Matrines
chemical_list: D000470:Alkaloids; D011807:Quinolizines; D014297:Trimethylsilyl Compounds; C586358:allomatrine; D000093842:Matrines