Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

被引：98

作者：

Chu, HW ^{[1
]}

Wu, HT ^{[1
]}

Lee, YJ ^{[1
]}

机构：

[1] Natl Changhua Univ Educ, Dept Chem, Changhua 50058, Taiwan

来源：

TETRAHEDRON | 2004年 / 60卷 / 11期

关键词：

flavones; hydroxylation; dioxirane;

D O I：

10.1016/j.tet.2004.01.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3',4',5,6,7,8-heptamethoxyflavone, quercetin and its derivatives were synthesized. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2647 / 2655

页数：9

共 53 条

[1] SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS [J].

ADAM, W ;

CHAN, YY ;

CREMER, D ;

GAUSS, J ;

SCHEUTZOW, D ;

SCHINDLER, M .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2800-2803

[2] DIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES [J].

ADAM, W ;

HADJIARAPOGLOU, L ;

SMERZ, A .

CHEMISCHE BERICHTE, 1991, 124 (01) :227-232

[3] EPOXIDATION OF FLAVONES BY DIMETHYLDIOXIRANE [J].

ADAM, W ;

GOLSCH, D ;

HADJIARAPOGLOU, L ;

PATONAY, T .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (26) :7292-7297

[4] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].

ADAM, W ;

CURCI, R ;

EDWARDS, JO .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211

[5]

ADAM W, 1994, SYNTHESIS-STUTTGART, V8, P560

[6]

ANJANEYULU ASR, 1981, INDIAN J CHEM B, V20, P87

[7] FLAVONOIDS OF MADHUCA BUTYRACEA NUT-SHELL [J].

AWASTHI, YC ;

MITRA, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (07) :2636-&

[8]

BABBER S, 1987, INDIAN J CHEM B, V26, P797

[9] FLAVONOIDS OF CHROMOLAENA-ODORATA [J].

BARUA, RN ;

SHARMA, RP ;

THYAGARAJAN, G ;

HERTZ, W .

PHYTOCHEMISTRY, 1978, 17 (10) :1807-1808

[10]

Belousov M. V., 1998, CHEM NAT COMPD, V34, P510

← 1 2 3 4 5 6 →