title: Different modes of cyclization in zoanthamine alkaloid system, bisaminal versus spiroketal formation.
abstract: Bisaminal cyclization in the zoanthamine alkaloid system was strongly affected by the stereochemistry of the C4 methyl. While cyclization of the (4S)-methyl precursor gave only a bisaminal compound, cyclization of the (4R)-methyl isomer produced both spiroketal and bisaminal products.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.
authors.forename: Takahiro
authors.initials: T
authors.lastname: Nakajima
authors.forename: Daisuke
authors.initials: D
authors.lastname: Yamashita
authors.forename: Kaname
authors.initials: K
authors.lastname: Suzuki
authors.forename: Atsuo
authors.initials: A
authors.lastname: Nakazaki
authors.forename: Takahiro
authors.initials: T
authors.lastname: Suzuki
authors.forename: Susumu
authors.initials: S
authors.lastname: Kobayashi
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D001381:Azepines / Q000737:chemistry*; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001381:Azepines; D005663:Furans; D006576:Heterocyclic Compounds, 4 or More Rings; D011804:Quinolines; D013141:Spiro Compounds; C520774:spiroketal; C542309:zoanthamine