Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins

被引：31
|
作者：
Maes, Dominick [1 ]
Riveiro, Maria Eugenia [2 ,3 ]
Shayo, Carina [2 ]
Davio, Carlos [3 ]
Debenedetti, Silvia [4 ]
De Kimpe, Norbert [1 ]
机构：
[1] Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium
[2] Inst Biol & Med Expt, RA-1428 Buenos Aires, DF, Argentina
[3] Univ Buenos Aires, Fac Farm & Bioquim, Lab Radioisotopos, RA-1113 Buenos Aires, DF, Argentina
[4] Natl Univ La Plata, Fac Ciencias Exactas, Catedra Farmacognosia, RA-1900 La Plata, Argentina
来源：
TETRAHEDRON | 2008年 / 64卷 / 19期
关键词：
coumarins; natural products; Wittig reaction; total synthesis;
D O I：
10.1016/j.tet.2008.02.059
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of five naturally occurring polyoxygenated coumarins is described. It concerns two 5,6,7-trioxygenated coumarins, i.e., 6-hydroxy-5,7-dimethoxycoumarin (fraxinol) 1 and 5,6,7-trimethoxycoumarin 2, and three 5,7,8-trioxygenated coumarins, i.e., 8-hydroxy-5,7-dimethoxycoumarin (leptodactylone) 3, 5,7,8-trimethoxycoumarin 4 and 8-(3-methyl-2-butenyloxy)-5,7-dimethoxycoumarin (artanin) 5. Key feature of the synthetic pathway is the synthesis of suitable tetraoxygenated benzaldehydes, which are then converted to the corresponding coumarins via a Wittig reaction. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4438 / 4443
页数：6
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