Synthesis of new furan derivatives and 4-hydroxy aldehydes from 4-hydroxy 1-enol ethers

被引:9
|
作者
Hölemann, A [1 ]
Reissig, HU [1 ]
机构
[1] Free Univ Berlin, Inst Chem, D-14195 Berlin, Germany
来源
SYNTHESIS-STUTTGART | 2004年 / 12期
关键词
enol ethers; gamma-lactols; gamma-lactones; tetrahydrofuran derivatives; aldehydes;
D O I
10.1055/s-2004-829175
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Starting from 4-hydroxy 1-enol ethers 3 different gamma-lactols 4 were successfully prepared by acidic hydrolysis. Subsequent oxidation of 4 with pyridinium chlorochromate (PCC) led to gamma-lactones 6 in good to excellent overall yields. Treatment of gamma-lactols 4 with silylated nucleophiles 7 in the presence of Lewis acids afforded substituted tetrahydrofuran derivatives 8 in good to excellent yields. Additionally, different functionalized aldehydes 12, 13, and 14 were prepared employing the TBS-protected enol ether 11 as precursor. All these transformations demonstrate the synthetic versatility of compounds 3.
引用
收藏
页码:1963 / 1970
页数:8
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