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The reaction of methyl isoferulate with FeCl3 or Ag2O—hypothesis on the biosynthesis of lithospermic acids and related nor and neolignans
Tetrahedron Letters ( IF 1.5 ) Pub Date : 14 April 2003 , DOI: 10.1016/s0040-4039(03)00584-7
Philippe Cotelle , Hervé Vezin

Methyl isoferulate reacts with FeCl3 to give (2-6) dimer 3 (6-6) dimer 4 and (6-O-3) dimer 5 in low yields, whereas it reacts with Ag2O leading to (2-O-3) dimer 6 and (6-O-3, 2-O-3) trimer 7. By comparison with literature data, we suggest that the biosynthesis of lithospermic acids and related nor and neolignans that possess a β-2 bond may be due to the cross dimerisation of ferulate radical on isoferulate.

中文翻译:

异亚硫酸甲酯与FeCl 3或Ag 2 O的反应假说对精子酸及其相关的正,新木脂素的生物合成

异亚硫酸甲酯与FeCl 3反应以低收率得到(2-6)二聚体3(6-6)二聚体4和(6-O-3)二聚体5,而与Ag 2 O反应生成(2-O- 3)二聚体6和(6-O-3,2-O-3)三聚体7。通过与文献数据比较,我们认为具有β-2键的紫精酸以及相关的nor和neolignans的生物合成可能是由于阿魏酸酯上阿魏酸酯基的交叉二聚作用。
更新日期:2017-01-31
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