title: Brønsted acid assisted activation of imide carbonyl group: regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine.
abstract: Activation of imide carbonyl group with trifluoromethanesulfonic acid facilitates the intramolecular cyclization of phenethylphthalimides to give a fused isoindoloisoquinolinone skeleton. The first one pot regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine has been successfully executed using this methodology.
authors.affiliation: Department of Chemistry, Pondicherry University, Puducherry, 605 014, India.
authors.forename: Jayaraman
authors.initials: J
authors.lastname: Selvakumar
authors.forename: Chinnasamy Ramaraj
authors.initials: CR
authors.lastname: Ramanathan
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D003500:Cyclization; D007094:Imides / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010797:Phthalimides / Q000737:chemistry; D015363:Quinolones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D007094:Imides; D007211:Indoles; D008698:Mesylates; D010797:Phthalimides; D015363:Quinolones; C012077:trifluoromethanesulfonic acid