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

共 50 条

[1] Theoretical study and vibrational spectroscopy of two 5,6,7-trioxygenated coumarins
Franca, Carlos A.
Baro, Ana C. Gonzalez
Diez, Reinaldo Pis
JOURNAL OF MOLECULAR STRUCTURE, 2007, 843 (1-3) : 57 - 65
[2] Preparation of (±)-5,6,7-trioxygenated dihydroflavonols and evaluation of their superoxide radical scavenging activity
Gong, JX
Bin Feng, Y
Wang, F
Wang, YG
Li, HB
Wu, YH
Hao, XJ
Wu, XM
Bai, H
Stöckigt, J
Zhao, Y
CHINESE CHEMICAL LETTERS, 2006, 17 (04) : 449 - 452
[3] Preparation of (±)-5,6,7-Trioxygenated Dihydroflavonols and Evaluation of their Superoxide Radical Scavenging Activity
Joachim STCKIGT
ChineseChemicalLetters, 2006, (04) : 449 - 452
[4] Chemoenzymatic Total Synthesis of a Naturally Occurring (5-5′)/(8′-O-4") Dehydrotrimer of Ferulic Acid
Mouterde, Louis M. M.
Flourat, Amandine L.
Cannet, Molly M. M.
Ducrot, Paul-Henri
Allais, Florent
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (01) : 173 - 179
[5] First Total Synthesis of a Naturally Occurring Iodinated 5′-Deoxyxylofuranosyl Marine Nucleoside
Sun, Jianyun
Dou, Yanhui
Ding, Haixin
Yang, Ruchun
Sun, Qi
Xiao, Qiang
MARINE DRUGS, 2012, 10 (04): : 881 - 889
[6] Synthesis of virgatol and virgatenol, two naturally occurring coumarins from Pterocaulon virgatum (L.) DC, and 7-(2,3-epoxy-3-methylbutoxy)-6-methoxycoumarin, isolated from Conyza obscura DC
Demyttenaere, J
Vervisch, S
Debenedetti, S
Coussio, J
Maes, D
De Kimpe, N
SYNTHESIS-STUTTGART, 2004, (11): : 1844 - 1848
[7] Synthesis and anti-proliferative activities of 5,6,7-trimethoxyflavones and their derivatives
Su, Liang
Li, Wei
Liu, Kexiong
Wang, Qiuan
NATURAL PRODUCT RESEARCH, 2022, 36 (16) : 4070 - 4075
[8] First total synthesis of a naturally occurring nucleoside disulfide: 9-(5′-Deoxy-5′-thio-β-D-xylofuranosyl)adenine disulfide
Ding, Hai Xin
Da, Ling Cui
Yang, Ru Chun
Cao, Ban Peng
Sun, Qi
Xiao, Qiang
CHINESE CHEMICAL LETTERS, 2012, 23 (09) : 996 - 998
[9] First total synthesis of a naturally occurring nucleoside disulfide:9-(5'-Deoxy-5'-thio-β-D-xylofuranosyl)adenine disulfide
Hai Xin Ding
Chinese Chemical Letters, 2012, (09) : 996 - 998
[10] Modified coumarins. 6. Synthesis of substituted 5,6-benzopsoralens
Garazd, YL
Ogorodniichuk, AS
Garazd, MM
Khilya, VP
CHEMISTRY OF NATURAL COMPOUNDS, 2002, 38 (05) : 424 - 433

← 1 2 3 4 5 →