title: Diversification of monoterpene indole alkaloid analogs through cross-coupling.
abstract: Catharanthus roseus monoterpene indole alkaloid analogs have been produced via a combination of biosynthetic and chemical strategies. Specifically, introduction of a chemical handle-a chlorine or a bromine-into the target molecule by mutasynthesis, followed by postbiosynthetic chemical derivatization using Pd-catalyzed Suzuki-Miyaura cross-coupling reactions robustly afforded aryl and heteroaryl analogs of these alkaloids.
authors.affiliation: Massachusetts Institute of Technology, Department of Chemistry, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.
authors.forename: Weerawat
authors.initials: W
authors.lastname: Runguphan
authors.forename: Sarah E
authors.initials: SE
authors.lastname: O'Connor
mesh_terms: D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D002713:Chlorine / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D003432:Cross-Linking Reagents; D006571:Heterocyclic Compounds; D026121:Indole Alkaloids; D039821:Monoterpenes; D002713:Chlorine; D001966:Bromine