title: Synthesis of (-)-epi-indolactam V by an intramolecular Buchwald-Hartwig C-N coupling cyclization reaction.
abstract: The synthetic efforts toward the concise synthesis of (-)-indolactam V from simple and commercially available starting materials using palladium- and copper-catalyzed intramolecular N-arylation strategy for the elaboration of the requisite nine-membered lactam ring as the key step are described. The incorporation of a turn-inducing structural element along the linear precursor was fundamental to achieve the heterocyclization step as well as obtain the correct regio- and chemoselectivity. The stereoselective nature in the C-N coupling cyclization reaction is interpreted in terms of minimization of allylic strain at the transition state for the palladium-amido complex formation. Meanwhile, the synthesis of the (-)-epi-indolactam V and its enantiomer have been accomplished.
authors.affiliation: Department of Biomolecular Sciences, University of Urbino Carlo Bo, Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
authors.forename: Michele
authors.initials: M
authors.lastname: Mari
authors.forename: Francesca
authors.initials: F
authors.lastname: Bartoccini
authors.forename: Giovanni
authors.initials: G
authors.lastname: Piersanti
mesh_terms: D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D007769:Lactams; C043969:indolactam V