A Convenient Synthesis of Pyranoid Ene Lactones from Phenyl Glycosyl Sulfones
- 1 January 1990
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1990 (10) , 875-877
- https://doi.org/10.1055/s-1990-27038
Abstract
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.Keywords
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