title: Oxidative Furan-to-Indole Rearrangement. Synthesis of 2-(2-Acylvinyl)indoles and Flinderole C Analogues.
abstract: Oxidative rearrangement of 2-(2-aminobenzyl)furans affording 2-(2-acylvinyl)indoles in a stereocontrolled manner in good-to-excellent yields has been developed. Thus, (2-aminobenzyl)furans with electron-releasing alkoxy substituents in the phenyl group form only E-isomers of 2-(2-acylvinyl)indoles. Conversely, substrates without such substituents produce target products as Z-isomers exclusively. A short diastereoselective method for the transformation of the obtained 2-(2-acylvinyl)indoles into antimalarial bisindole alkaloid flinderole A-C analogues has been developed.
authors.affiliation: Department of Chemistry, Perm State University , Bukireva st. 15, Perm 614990, Russia.
authors.forename: Anton S
authors.initials: AS
authors.lastname: Makarov
authors.affiliation: Department of Chemistry, Perm State University , Bukireva st. 15, Perm 614990, Russia.|Institute of Technical Chemistry UrB RAS, Academika Koroleva st. 3, Perm 614013, Russia.
authors.forename: Anton A
authors.initials: AA
authors.lastname: Merkushev
authors.affiliation: Department of Chemistry, Perm State University , Bukireva st. 15, Perm 614990, Russia.
authors.forename: Maxim G
authors.initials: MG
authors.lastname: Uchuskin
authors.affiliation: Department of Chemistry, M.V. Lomonosov Moscow State University , Leninskie gory 1-3, Moscow 119991, Russia.|Laboratory of Chemical Synthesis, Federal Research Center of Pediatric Hematology, Oncology and Immunology , Samory Mashela 1, Moscow 117997, Russia.
authors.forename: Igor V
authors.initials: IV
authors.lastname: Trushkov