Ultrasound-assisted convenient synthesis of hypolipidemic active natural methoxylated (E)-arylalkenes and arylalkanones

被引：43

作者：

Joshi, BP ^{[1
]}

Sharma, A ^{[1
]}

Sinha, AK ^{[1
]}

机构：

[1] Inst Himalayan Bioresource Technol, Nat Plant Prod Div, Palampur 176061, Himachal Prades, India

来源：

TETRAHEDRON | 2005年 / 61卷 / 12期

关键词：

hypolipidemic; ultrasound; (E)-arylalkenes; arylalkanones; DDQ;

D O I：

10.1016/j.tet.2005.01.071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An ultrasound-assisted convenient method was developed for the conversion of toxic methoxylated cis-isomer of arylalkenes into its hypolipidemic active trans-isomer. Treatment of cis-isomer or mixture of all three isomers (1a-1j) with ammonium formate and 10% Pd/C gave arylalkanes (2a-2j), which upon oxidation with DDQ in anhydrous dioxane containing a little amount of silica gel, provided (E)-arylalkenes (3a-3g) in 42-72% yield depending upon the substituents attached at the aryl ring. The same method, upon addition of a few drops of water, provided hypolipidemic active arylalkanones (3h-3j) in 59-65% yield. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3075 / 3080

页数：6

共 58 条

[1] Hypolipidemic effects of modified psyllium preparations
Allen, KGD
Bristow, SJ
Yu, LL
[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (16) : 4998 - 5003
[2] BAMBANG WN, 1996, PHYTOCHEMISTRY, V41, P129
[3] A polymer-supported iridium catalyst for the stereoselective isomerisation of double bonds
Baxendale, IR
Lee, AL
Ley, SV
[J]. SYNLETT, 2002, (03) : 516 - 518
[4] The protective action of ethanolic ginger (Zingiber officinale) extract in cholesterol fed rabbits
Bhandari, U
Sharma, JN
Zafar, R
[J]. JOURNAL OF ETHNOPHARMACOLOGY, 1998, 61 (02) : 167 - 171
[5] Buckingham J., 1994, DICT NATURAL PRODUCT
[6] BUCKINGHAM J, 1982, DICT ORGANIC COMPOUN
[7] TRANS ALKENES BY STEREOSELECTIVE REDUCTION OF ALPHA-PH2PO KETONES - E-ISOSAFFROLE, E-ANETHOLE, AND FENICULIN
BUSS, AD
MASON, R
WARREN, S
[J]. TETRAHEDRON LETTERS, 1983, 24 (47) : 5293 - 5296
[8] CESKA R, 2004, INT C SER, V1262, P458
[9] Hibiscus sabdariffa extract inhibits the development of atherosclerosis in cholesterol-fed rabbits
Chen, CC
Hsu, JD
Wang, SF
Chiang, HC
Yang, MY
Kao, ES
Ho, YC
Wang, CJ
[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (18) : 5472 - 5477
[10] New chemical structures of hypolipidemic and antiplatelet activity
Chilmonczyk, Z
Siluk, D
Kaliszan, R
Lozowicka, B
Poplawski, J
Filipek, S
[J]. PURE AND APPLIED CHEMISTRY, 2001, 73 (09) : 1445 - 1458

← 1 2 3 4 5 6 →