Oxidative cleavage of 3-alkoxy-2,5-dihydrofurans and its application to the de novo synthesis of rare monosaccharides as exemplified by L-cymarose

被引:38
作者
Brasholz, Malte [1 ]
Reissig, Hans-Ulrich [1 ]
机构
[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
关键词
allenes; carbohydrates; oxidation; oxygen heterocycles; reduction;
D O I
10.1002/anie.200604078
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) 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). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1634 / 1637
页数:4
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