Synthesis of nonadjacently linked tetrahydrofurans: an iodoetherification and olefin metathesis approach.
[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.
Zhu
Lei
L
Department of Chemistry, Hunter College, 695 Park Avenue, New York, New York 10021, USA.
Mootoo
David R
DR
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
D000475:Alkenes; D000970:Antineoplastic Agents; D004988:Ethers, Cyclic; D005663:Furans; D007783:Lactones; C087002:bullatencin