title: A total synthesis of the antitumour macrolide rhizoxin D.
abstract: An enantioselective synthesis of rhizoxin D, isolated from the plant pathogenic fungus Rhizopus chinensis, is described. The overall strategy is based on elaboration of the delta-lactone-substituted vinyl stannane and the phosphonate-substituted vinyl iodide, followed by their coupling to the core 16-membered macrolide via a sequential intermolecular Horner-Wadsworth-Emmons olefination, leading to (50), and by an intramolecular Stille reaction. The triene oxazole-containing side chain in rhizoxin D is then introduced using the phosphine oxide in an E-selective Horner-Wittig reaction with the macrolide aldehyde.
authors.affiliation: School of Chemistry, The University of Nottingham, Nottingham, UK, NG7 2RD.
authors.forename: Ian S
authors.initials: IS
authors.lastname: Mitchell
authors.forename: Gerald
authors.initials: G
authors.lastname: Pattenden
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Stonehouse
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000970:Antineoplastic Agents; D007783:Lactones; D018942:Macrolides; C479980:rhizoxin D