Total synthesis of (S)-(+)-tylophorine via enantioselective intramolecular alkene carboamination.
The enantioselective synthesis of (S)-(+)-tylophorine, a potent cancer cell growth inhibitor, has been accomplished in eight steps from commercially available 3,4-dimethoxybenzyl alcohol. A copper (II)-catalyzed enantioselective intramolecular alkene carboamination was employed as the key step to construct the chiral indolizidine ring.
Zeng
Wei
W
Department of Chemistry, The University at Buffalo, The State University of New York, Buffalo, New York 14260, USA.
Chemler
Sherry R
SR
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D001688:Biological Products / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000475:Alkenes; D001688:Biological Products; D007212:Indolizines; D010616:Phenanthrenes; C004218:tylophorine