title: Synthesis of nonadjacently linked tetrahydrofurans: an iodoetherification and olefin metathesis approach.
abstract: [reaction: see text] A convergent approach to the synthesis of the bis-tetrahydrofuran (THF) components of the nonadjacently linked THF-containing acetogenins is illustrated in the synthesis of 2, a potential intermediate for the antitumor agent bullatanocin (squamostatin C). The plan centers on the olefin cross-metathesis of THF allylic alcohol derivatives 3 and 4 as the key segment coupling step and the assembly of 3 and 4 through the iodoetherification of 1,2-O-isopropylidene-5-alkene precursors.
authors.affiliation: Department of Chemistry, Hunter College, 695 Park Avenue, New York, New York 10021, USA.
authors.forename: Lei
authors.initials: L
authors.lastname: Zhu
authors.forename: David R
authors.initials: DR
authors.lastname: Mootoo
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D002384:Catalysis; D004988:Ethers, Cyclic / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000970:Antineoplastic Agents; D004988:Ethers, Cyclic; D005663:Furans; D007783:Lactones; C087002:bullatencin