title: Synthetic studies of the zoanthamine alkaloids: total synthesis of zoanthenol based on an isoaromatization strategy.
abstract: The total synthesis of zoanthenol, a unique aromatic member of the zoanthamine alkaloids, which has exhibited potent anti-platelet activities on human platelet aggregation, is described in full detail. The key step involves a Brønsted acid-promoted isoaromatization in the AB ring system to install the crucial aromatic ring. We have not only succeeded in the first total synthesis of zoanthenol, but also established an alternative efficient synthetic route from the commercially available norzoanthamine hydrochloride to zoanthenol.
authors.affiliation: Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.
authors.forename: Fumihiko
authors.initials: F
authors.lastname: Yoshimura
authors.forename: Yu
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Keiji
authors.initials: K
authors.lastname: Tanino
authors.forename: Masaaki
authors.initials: M
authors.lastname: Miyashita
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001381:Azepines / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D010084:Oxidation-Reduction; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D001381:Azepines; D006576:Heterocyclic Compounds, 4 or More Rings; D006572:Heterocyclic Compounds, Bridged-Ring; D010975:Platelet Aggregation Inhibitors; D011804:Quinolines; C542309:zoanthamine; C457061:zoanthenol; C400280:norzoanthamine