title: Stereoselective synthesis of a natural product inspired tetrahydroindolo[2,3-a]-quinolizine compound library.
abstract: A natural product-inspired synthesis of a compound collection embodying the tetrahydroindolo[2,3-a]quinolizine scaffold was established with a five step synthesis route. An imino-Diels-Alder reaction between Danishefsky's diene and the iminoesters derived from tryptamines was used as a key reaction. Reductive amination of the ketone function and amide synthesis with the carboxylic acid derived from the ethyl ester, were used to decorate the core scaffold. Thus a compound library of 530 tetrahydroindolo[2,3-a]quinolizines was generated and submitted to European lead factory consortium for various biological screenings.
authors: Max-Planck-Institut für molekulare Physiologie, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany.
authors: Muthukumar G
authors: MG
authors: Sankar
authors: Medicinal Chemistry, Taros Chemicals GmbH & Co. KG, Emil-Figge-Str. 76a, 44227 Dortmund, Germany.
authors: Luca
authors: L
authors: Mantilli
authors: Medicinal Chemistry, Taros Chemicals GmbH & Co. KG, Emil-Figge-Str. 76a, 44227 Dortmund, Germany.
authors: James
authors: J
authors: Bull
authors: Medicinal Chemistry, Taros Chemicals GmbH & Co. KG, Emil-Figge-Str. 76a, 44227 Dortmund, Germany.
authors: Fabrizio
authors: F
authors: Giordanetto
authors: Fakultät für Chemie und Chemische Biologie, Technische Universität, Dortmund, 44221 Dortmund, Germany.
authors: Jonathan O
authors: JO
authors: Bauer
authors: Fakultät für Chemie und Chemische Biologie, Technische Universität, Dortmund, 44221 Dortmund, Germany.
authors: Carsten
authors: C
authors: Strohmann
authors: Max-Planck-Institut für molekulare Physiologie, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany; Fakultät für Chemie und Chemische Biologie, Technische Universität, Dortmund, 44221 Dortmund, Germany. Electronic address: herbert.waldmann@mpi-dortmund.mpg.de.
authors: Herbert
authors: H
authors: Waldmann
authors: Max-Planck-Institut für molekulare Physiologie, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany. Electronic address: kamal.kumar@mpi-dortmund.mpg.de.
authors: Kamal
authors: K
authors: Kumar
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D061565:Cycloaddition Reaction; D055808:Drug Discovery; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D011807:Quinolizines / Q000737:chemistry*; D054852:Small Molecule Libraries / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D007211:Indoles; D011807:Quinolizines; D054852:Small Molecule Libraries
keywords: Compound library; Imino-Diels–Alder reaction; Indole alkaloids; Indoloquinolizines; Stereoselective reactions