title: Total synthesis of a pyrroloindoloquinazoline alkaloid.
abstract: A highly concise stereoselective synthesis of a newly identified alkaloid with a pyrroloindoloquinazoline skeleton has been achieved. To this end, a chiral auxiliary mediated asymmetric acetate aldol reaction on tryptanthrin was explored and the resulting adduct was converted to the product by a novel one-pot reductive cyclization/transamidation using NiCl2·6H2O/NaBH4 in methanol.
authors.affiliation: Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Sector 67, Mohali, Punjab 160062, India.
authors.forename: Digvijay
authors.initials: D
authors.lastname: Gahtory
authors.forename: Mangilal
authors.initials: M
authors.lastname: Chouhan
authors.forename: Ratnesh
authors.initials: R
authors.lastname: Sharma
authors.forename: Vipin A
authors.initials: VA
authors.lastname: Nair
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D007211:Indoles; D011758:Pyrroles; D011799:Quinazolines