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

被引：44

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 [J].

Allen, KGD ;

Bristow, SJ ;

Yu, LL .

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 [J].

Baxendale, IR ;

Lee, AL ;

Ley, SV .

SYNLETT, 2002, (03) :516-518

[4] The protective action of ethanolic ginger (Zingiber officinale) extract in cholesterol fed rabbits [J].

Bhandari, U ;

Sharma, JN ;

Zafar, R .

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 [J].

BUSS, AD ;

MASON, R ;

WARREN, S .

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 [J].

Chen, CC ;

Hsu, JD ;

Wang, SF ;

Chiang, HC ;

Yang, MY ;

Kao, ES ;

Ho, YC ;

Wang, CJ .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (18) :5472-5477

[10] New chemical structures of hypolipidemic and antiplatelet activity [J].

Chilmonczyk, Z ;

Siluk, D ;

Kaliszan, R ;

Lozowicka, B ;

Poplawski, J ;

Filipek, S .

PURE AND APPLIED CHEMISTRY, 2001, 73 (09) :1445-1458

← 1 2 3 4 5 6 →