title: Expanding the scope of Mn(OAc)3-mediated cyclizations: synthesis of the tetracyclic core of tronocarpine.
abstract: Pyrroles, indoles, and surprisingly, indolines, when equipped with a pendant malonyl group on the nitrogen atom, were effective substrates in a Mn(III)-mediated oxidative cyclization reaction, yielding the 1,2-annulated products in good to excellent yields. When indole acetonitrile was used as a substrate this method provided a rapid synthesis of a tetracyclic tronocarpine subunit.
authors.affiliation: Department of Chemistry, University of Western Ontario, London, Ontario, Canada N6A 5B7.
authors.forename: Jakob
authors.initials: J
authors.lastname: Magolan
authors.forename: Michael A
authors.initials: MA
authors.lastname: Kerr
mesh_terms: D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D017895:Manganese Compounds / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D001381:Azepines; D026121:Indole Alkaloids; D017895:Manganese Compounds; C520942:tronocarpine