NMR Determination of the Absolute Configuration of an α-Exo-methylene-γ-lactone

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  • FUKUI Hiroki
    Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University
  • FUKUSHI Yukiharu
    Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University CREST, Japan Science and Technology Corporation
  • TAHARA Satoshi
    Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University CREST, Japan Science and Technology Corporation

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タイトル別名
  • NMR Determination of the Absolute Configuration of an .ALPHA.-Exo-methylene-.GAMMA.-lactone.
  • NMR Determination of the Absolute Configuration of an アルファ Exo methylene ガンマ lactone

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  Both the enantiomers of the axially chiral reagent, 2′-methoxy-1,1′-binaphthalene-2-carbohydroximoyl chloride (MBCC), were used to convert igalan, an α-exo-methylene-γ-lactone, to yield 4,5-dihydroisoxazoles. The absolute configuration of igalan was determined to be (3aR,5R,6R,7aR)-6-ethenylhexahydro-6-methyl-3-methylene-5-(1-methylethenyl)-2(3H)-benzofuranone (IUPAC name) on the basis of NOE correlations in these derivatives. The absolute configurations of other α-exo-methylene-γ-lactones can be determined by the same method.<br>

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