title: T3P-Promoted, Mild, One-Pot Syntheses of Constrained Polycyclic Lactam Dipeptide Analogues via Stereoselective Pictet-Spengler and Meyers Lactamization Reactions.
abstract: A new convenient, mild, one-pot procedure is described for the diastereoselective synthesis of constrained 7,5- and 7,6-fused azabicycloalkanes. Using 2-formyl-L-tryptophan and 2-formyl-l-phenylalanine as bielectrophilic building blocks, T3P-mediated Pictet-Spengler and Meyers lactamization reactions were developed to present chiral and polycyclic aminoindolo- and aminobenzazepinone compounds in excellent yields. The conformationally constrained compounds can serve as templates for peptidomimetic research or polyheterocyclic privileged scaffolds.
authors: Research Group of Organic Chemistry, Departments of Chemistry and Bio-Engineering Sciences, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium.
authors: Mouhamad
authors: M
authors: Jida
authors: Research Group of Organic Chemistry, Departments of Chemistry and Bio-Engineering Sciences, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium.
authors: Olivier
authors: O
authors: Van der Poorten
authors: Research Group of Organic Chemistry, Departments of Chemistry and Bio-Engineering Sciences, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium.
authors: Karel
authors: K
authors: Guillemyn
authors: Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka Strasse 44/52, 01-224 Warsaw, Poland.
authors: Zofia
authors: Z
authors: Urbanczyk-Lipkowska
authors: Research Group of Organic Chemistry, Departments of Chemistry and Bio-Engineering Sciences, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium.
authors: Dirk
authors: D
authors: Tourwé
authors: Research Group of Organic Chemistry, Departments of Chemistry and Bio-Engineering Sciences, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium.
authors: Steven
authors: S
authors: Ballet
mesh_terms: D000812:Anhydrides / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D010649:Phenylalanine; D013237:Stereoisomerism
chemical_list: D000812:Anhydrides; D004151:Dipeptides; D007769:Lactams; D063065:Organophosphonates; C540935:propylphosphonic acid anhydride; D010649:Phenylalanine