title: Total synthesis of ipomoeassin F.
abstract: The first total synthesis of ipomoeassin F was carried out using a convergent approach that relied upon the use of Schmidt glycosidation technology for the coupling of two suitably protected monosaccharide fragments. After two steps, ring-closing metathesis was used to form the macrocyclic ring, and seven more steps then furnished ipomoeassin F. In vitro inhibitory activity against a four-panel cell line showed low nanomolar inhibitory activity.
authors.affiliation: Department of Discovery Chemistry, Eisai Research Institute, 4 Corporate Drive, Andover, Massachusetts 01810, USA. maarten_postema@eri.eisai.com
authors.forename: Maarten H D
authors.initials: MH
authors.lastname: Postema
authors.forename: Karen
authors.initials: K
authors.lastname: TenDyke
authors.forename: James
authors.initials: J
authors.lastname: Cutter
authors.forename: Galina
authors.initials: G
authors.lastname: Kuznetsov
authors.forename: Qunli
authors.initials: Q
authors.lastname: Xu
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006031:Glycosylation; D006801:Humans; D027741:Ipomoea / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D001688:Biological Products; D006001:Glycoconjugates; C523857:ipomoeassin F