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

页码：4438 / 4443

页数：6

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