Total synthesis of (-)-acutumine.
The first total synthesis of the tetracyclic alkaloid (-)-acutumine is described. Key reactions include an asymmetric ketone allylation mediated by Nakamura's chiral allylzinc reagent, an anionic oxy-Cope rearrangement, and the Lewis acid-promoted cyclization of an amine onto an alpha,beta-unsaturated dimethyl ketal.
Li
Fang
F
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.
Tartakoff
Samuel S
SS
Castle
Steven L
SL
D000470:Alkaloids / Q000138:chemical synthesis*; D003500:Cyclization; D031603:Menispermum / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*
D000470:Alkaloids; D013141:Spiro Compounds; C442344:acutumine