title: Total synthesis of (+)-trans-dihydronarciclasine utilizing asymmetric conjugate addition.
abstract: A highly efficient short-step construction of the common phenanthridine skeleton of pancratistatin-class alkaloids was accomplished in enantiomerically pure form using chiral ligand-controlled asymmetric conjugate addition. The utility of the intermediate was demonstrated by the total synthesis of (+)-trans-dihydronarciclasine with mild oxidation from an amine to an amide as a key step.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo, Kyoto 606-8501, Japan.
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Yamada
authors.forename: Yuzo
authors.initials: Y
authors.lastname: Mogi
authors.forename: Magdi A
authors.initials: MA
authors.lastname: Mohamed
authors.forename: Kiyosei
authors.initials: K
authors.lastname: Takasu
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Tomioka
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D047151:Amaryllidaceae Alkaloids / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D007546:Isoquinolines / Q000737:chemistry; D015394:Molecular Structure; D010617:Phenanthridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D000577:Amides; D000588:Amines; D007546:Isoquinolines; D010617:Phenanthridines; C064338:dihydronarciclasine; C044997:pancratistatin