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Synthesis 1990; 1990(10): 875-877
DOI: 10.1055/s-1990-27038
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A Convenient Synthesis of Pyranoid Ene Lactones from Phenyl Glycosyl Sulfones

Dongxu Qiu* , Richard R. Schmidt
  • *Fakultät Chemie, Universität Konstanz, Postfach 5560, D-7750 Konstanz, Federal Republic of Germany
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Publication Date:
17 September 2002 (online)

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O-Benzyl protected pyranoid ene lactones (5,6-dihydro-2H/-pyran-2-ones) 4a-c, 8 were obtained in high yield in a two-step procedure. Treatment of the phenyl glycosyl sulfones 2a-d, 6, which were readily prepared from their corresponding sulfides, with lithium diisopropylamide (LDA) at -90°C afforded the elimination products 3a-c, 7. These intermediates were then treated with sodium methoxide in the presence of dicyclohexano-18-crown-6 to give the compounds 4a-c, 8.