Synthesis of (±)-oleocanthal via a tandem intramolecular Michael cyclization-HWE olefination

被引:26
作者
English, Brandon J. [1 ]
Williams, Robert M. [1 ,2 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
[2] Univ Colorado, Ctr Canc, Aurora, CO 80045 USA
基金
美国国家卫生研究院;
关键词
ALPHA PRODUCTION; IRIDOIDS; INHIBITION; POTENT;
D O I
10.1016/j.tetlet.2009.03.145
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of racemic oleocanthal has been accomplished in 11 steps from 1,3 propanediol by a key tandem intramolecular Michael cyclization-Horner-Wadsworth-Emmons olefination. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2713 / 2715
页数:3
相关论文
共 18 条
[1]   Phytochemistry - Ibuprofen-like activity in extra-virgin olive oil [J].
Beauchamp, GK ;
Keast, RSJ ;
Morel, D ;
Lin, JM ;
Pika, J ;
Han, Q ;
Lee, CH ;
Smith, AB ;
Breslin, PAS .
NATURE, 2005, 437 (7055) :45-46
[2]   Effects of some iridoids from plant origin on arachidonic acid metabolism in cellular systems [J].
Benito, PB ;
Lanza, AMD ;
Sen, AMS ;
Galindez, JD ;
Matellano, LF ;
Gómez, AS ;
Martínez, MJA .
PLANTA MEDICA, 2000, 66 (04) :324-328
[3]   Antiviral activity of seven iridoids, three saikosaponins and one phenylpropanoid glycoside extracted from Bupleurum rigidum and Scrophularia scorodonia [J].
Bermejo, P ;
Abad, MJ ;
Díaz, AM ;
Fernández, L ;
De Santos, J ;
Sanchez, S ;
Villaescusa, L ;
Carrasco, L ;
Irurzun, A .
PLANTA MEDICA, 2002, 68 (02) :106-110
[4]  
Boje K, 2003, PLANTA MED, V69, P820, DOI 10.1055/s-2003-43225
[5]   New iridoids from the medicinal-plant Barleria prionitis with potent activity against respiratory syncytial virus [J].
Chen, JL ;
Blanc, P ;
Stoddart, CA ;
Bogan, M ;
Rozhon, EJ ;
Parkinson, N ;
Ye, ZJ ;
Cooper, R ;
Balick, M ;
Nanakorn, W ;
Kernan, MR .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (10) :1295-1297
[6]  
Chrubasik S, 1999, EUR J ANAESTH, V16, P118
[7]   Complement-inhibiting iridoids from Morinda morindoides [J].
Cimanga, K ;
Hermans, N ;
Apers, S ;
Van Miert, S ;
Van den Heuvel, H ;
Claeys, M ;
Pieters, L ;
Vlietinck, A .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (01) :97-102
[8]   The preparation of α-alkylidene-γ-butyrolactones using a telescoped intramolecular Michael/olefination (TIMO) sequence:: Synthesis of (+)-paeonilactone B [J].
Edwards, Michael G. ;
Kenworthy, Martin N. ;
Kitson, Russell R. A. ;
Perry, Alexis ;
Scott, Mark S. ;
Whitwood, Adrian C. ;
Taylor, Richard J. K. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (28) :4769-4783
[9]   The telescoped intramolecular Michael/olefination (TIMO) approach to α-alkylidene-γ-butyrolactones:: Synthesis of (+)-paeonilactone B [J].
Edwards, Michael G. ;
Kenworthy, Martin N. ;
Kitson, Russell R. A. ;
Scott, Mark S. ;
Taylor, Richard J. K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1935-1937
[10]  
Ju HK, 2003, PLANTA MED, V69, P950, DOI 10.1055/s-2003-45107