title: Synthetic study of (-)-norzoanthamine: construction of the ABC ring moiety.
abstract: Throw your hat in the ring: A highly diastereoselective synthesis of the ABC rings of (-)-norzoanthamine has been achieved starting from the (-)-Hajos-Parrish ketone (see scheme). Three asymmetric quaternary carbon centers on the C ring were constructed by a 1,4-addition, and an intramolecular Diels-Alder reaction provided a trans-decalin scaffold on the AB rings.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba, Japan.
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Murata
authors.forename: Daisuke
authors.initials: D
authors.lastname: Yamashita
authors.forename: Katsushi
authors.initials: K
authors.lastname: Kitahara
authors.forename: Yohei
authors.initials: Y
authors.lastname: Minasako
authors.forename: Atsuo
authors.initials: A
authors.lastname: Nakazaki
authors.forename: Susumu
authors.initials: S
authors.lastname: Kobayashi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001381:Azepines; D006576:Heterocyclic Compounds, 4 or More Rings; D011804:Quinolines; C400280:norzoanthamine