title: A concise total synthesis of the natural carbazole clauraila A.
abstract: A short and efficient total synthesis of naturally occurring carbazole clauraila A (1) is described. The approach is designed on the basis of the key regioselective Diels-Alder reaction of the properly substituted exo-2-oxazolidinone diene 3 with acrolein (4) to give the corresponding adduct 2. The latter is converted to functionalised diarylamine 8, which is cyclised to the desired carbazole 1 through a Pd-promoted or -catalysed double C-H bond activation process in a fairly good overall yield.
authors.affiliation: a Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas , Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala , 11340 , México , D.F. Mexico.
authors.forename: Rafael
authors.initials: R
authors.lastname: Bautista
authors.forename: Adriana
authors.initials: A
authors.lastname: Benavides
authors.forename: Hugo A
authors.initials: HA
authors.lastname: Jiménez-Vázquez
authors.forename: Joaquín
authors.initials: J
authors.lastname: Tamariz
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D002227:Carbazoles; C570570:clauraila A; C041514:carbazole