title: β-Selective C-H arylation of pyrroles leading to concise syntheses of lamellarins C and I.
abstract: The first general β-selective C-H arylation of pyrroles has been developed by using a rhodium catalyst. This C-H arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of pyrrole-derived natural products and pharmaceuticals. As such, we have successfully synthesized polycyclic marine pyrrole alkaloids, lamellarins C and I, by using this β-selective arylation of pyrroles with aryl iodides (C-H/C-I coupling) and a new double C-H/C-H coupling as key steps.
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University , Chikusa, Nagoya 464-8602, Japan.
authors.forename: Kirika
authors.initials: K
authors.lastname: Ueda
authors.forename: Kazuma
authors.initials: K
authors.lastname: Amaike
authors.forename: Richard M
authors.initials: RM
authors.lastname: Maceiczyk
authors.forename: Kenichiro
authors.initials: K
authors.lastname: Itami
authors.forename: Junichiro
authors.initials: J
authors.lastname: Yamaguchi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007454:Iodides / Q000138:chemical synthesis / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry
chemical_list: D000470:Alkaloids; D001688:Biological Products; D007454:Iodides; D011758:Pyrroles; C000602015:lamellarin C; C000602016:lamellarin I; D012238:Rhodium