title: Overturning indolyne regioselectivities and synthesis of indolactam V.
abstract: We report the design and synthesis of an indolyne that displays a reversal in regioselectivity, in both nucleophilic addition and cycloaddition reactions, compared to typical 4,5-indolynes. Our approach utilizes simple computations to predict regioselectivity in reactions of unsymmetrical arynes. With this methodology, novel benzenoid-substituted indoles can be accessed with significant regiocontrol. Furthermore, the technology provides an unconventional tactic for the synthesis of C4-substituted indole alkaloids, as demonstrated by a synthesis of indolactam V.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
authors.forename: Sarah M
authors.initials: SM
authors.lastname: Bronner
authors.forename: Adam E
authors.initials: AE
authors.lastname: Goetz
authors.forename: Neil K
authors.initials: NK
authors.lastname: Garg
mesh_terms: D007211:Indoles / Q000138:chemical synthesis*; D007769:Lactams / Q000138:chemical synthesis*; D008958:Models, Molecular
chemical_list: D007211:Indoles; D007769:Lactams; C043969:indolactam V