title: A concise total synthesis of (±)-trigonoliimine B.
abstract: Trigonoliimine B, a hexacyclic alkaloid, is synthesized in seven steps from simple starting materials. The synthesis features the use of an α-isocyanoacetate as a glycine template for the preparation of an α,α-disubstituted α-amino ester that is appropriately functionalized for the construction of C, D, and E rings. Sulfolane was found to be the solvent of choice for the unprecedented Bischler-Napieralski reaction implemented for the construction of a seven-membered ring with concurrent formation of an exo-imine function.
authors.affiliation: Institut of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, CH-1015 Lausanne, Switzerland.
authors.forename: Thomas
authors.initials: T
authors.lastname: Buyck
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000586:Amination; D004952:Esters / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D015394:Molecular Structure
chemical_list: D004952:Esters; D026121:Indole Alkaloids; C551378:trigonoliimine B