title: Convergent synthesis of (-)-quinocarcin based on the combination of Sonogashira coupling and gold(I)-catalyzed 6-endo-dig hydroamination.
abstract: The total synthesis of the pentacyclic tetrahydroisoquinoline alkaloid quinocarcin, which possesses intriguing structural and biological features, has been achieved through a gold(I)-catalyzed regioselective hydroamination reaction. It is noteworthy that the regioselectivity of the intramolecular hydroamination of an unsymmetrical alkyne could be completely switched through substrate control. Other key features of this synthesis include the highly stereoselective synthesis of 2,5-cis-pyrrolidine through the intramolecular amination of the bromoallene and the Lewis acid mediated ring opening of dihydrobenzofuran.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Chiba
authors.forename: Yuki
authors.initials: Y
authors.lastname: Sakai
authors.forename: Ayako
authors.initials: A
authors.lastname: Ohara
authors.forename: Shinya
authors.initials: S
authors.lastname: Oishi
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Fujii
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Ohno
mesh_terms: D000586:Amination; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002384:Catalysis; D006046:Gold; D007546:Isoquinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D007546:Isoquinolines; D006046:Gold; C038710:quinocarcin