title: Converting cycloalkanones into N-heterocycles: formal synthesis of (-)-gephyrotoxin 287C.
abstract: The photochemical rearrangement of N-activated lactams enables their ring contraction concomitant with the migration of a carbon onto a nitrogen atom. When coupled with the Beckmann rearrangement, this photochemical ring contraction converts cycloalkanones into N-heterocycles in a few steps and in a stereospecific manner. To showcase the method, we performed an efficient formal synthesis of (-)-gephyrotoxin 287C.
authors.affiliation: Département de Chimie, Université de Sherbrooke , Sherbrooke, Québec, Canada J1K 2R1.
authors.forename: Simon
authors.initials: S
authors.lastname: Pichette
authors.forename: Dana K
authors.initials: DK
authors.lastname: Winter
authors.forename: Jean
authors.initials: J
authors.lastname: Lessard
authors.forename: Claude
authors.initials: C
authors.lastname: Spino
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000470:Alkaloids; D006571:Heterocyclic Compounds; D007659:Ketones; C014569:gephyrotoxin