title: Synthesis of (±)-cis-clavicipitic acid by a Rh(I)-catalyzed intramolecular imine reaction.
abstract: A new and short synthesis of racemic cis-clavicipitic acid was achieved by taking advantage of the double nucleophilic character of indole-4-pinacolboronic ester. Key to the success of the synthesis were an efficient and selective C-3 indole Friedel-Crafts alkylation and the development of an unprecedented intramolecular rhodium-catalyzed 1,2-addition of an aryl pinacolboronic ester to an unactivated imine.
authors.affiliation: Department of Biomolecular Sciences, University of Urbino "Carlo Bo" , Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
authors.forename: Francesca
authors.initials: F
authors.lastname: Bartoccini
authors.forename: Mariangela
authors.initials: M
authors.lastname: Casoli
authors.forename: Michele
authors.initials: M
authors.lastname: Mari
authors.forename: Giovanni
authors.initials: G
authors.lastname: Piersanti
mesh_terms: D000478:Alkylation; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D004876:Ergot Alkaloids / Q000138:chemical synthesis*; D004952:Esters; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D004876:Ergot Alkaloids; D004952:Esters; D007097:Imines; D007211:Indoles; C524935:clavicipitic acid; C000594404:indole-4-pinacolboronic ester; C030374:indole; D012238:Rhodium