title: A tandem Friedel-Crafts based method for the construction of a tricyclic pyrroloquinoline skeleton and its application in the synthesis of ammosamide B.
abstract: A total synthesis of ammosamide B (2), a member of the pyrroloquinoline alkaloid family isolated from marine Streptomyces, is described. The characteristic core tricyclic structure of 2 was constructed using a novel, tandem Friedel-Crafts reaction sequence to transform the symmetric tetra-amino substituted benzene derivative 7 into the tricyclic pyrroloquinoline product 8, which serves as an important intermediate in the route to the synthesis of the target natural product.
authors.affiliation: Department of Biotechnology and Life Science, Faculty of Technology, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan.
authors.forename: Yohei
authors.initials: Y
authors.lastname: Takayama
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Yamada
authors.forename: Shinya
authors.initials: S
authors.lastname: Tatekabe
authors.forename: Kazuo
authors.initials: K
authors.lastname: Nagasawa
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*
chemical_list: D000577:Amides; D006575:Heterocyclic Compounds, 3-Ring; D011758:Pyrroles; D011804:Quinolines; C534623:ammosamide B; C410406:pyrroloquinoline