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Oxidative Cleavage of 3-Alkoxy-2,5-dihydrofurans and its Application to the De Novo Synthesis of Rare Monosaccharides as Exemplified by L-Cymarose


  • The authors thank the Fonds der Chemischen Industrie (PhD fellowship for M. B.) and the Schering AG for generous support.


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Donor-substituted α,β-unsaturated γ-keto aldehydes can be formed by the selective oxidative cleavage of 3-alkoxy-2,5-dihydrofurans. These 1,4-dicarbonyl compounds are highly suitable building blocks for the synthesis of rare sugars, for example, the dideoxypyranose L-cymarose (see scheme).

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