The Development of a General Strategy for the Synthesis of Tyramine-Based Natural Products by Using Continuous Flow Techniques

被引:31
作者
Achanta, Srinivas [1 ]
Liautard, Virginie [1 ]
Paugh, Robert [1 ]
Organ, Michael G. [1 ]
机构
[1] York Univ, Dept Chem, Toronto, ON M3J 1P3, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
flow chemistry; Heck reaction; microwave chemistry; tyramine; ORGANIC-SYNTHESIS MACOS; THIN-FILMS; CAPILLARIES; INHIBITOR; AMIDES; GOLD;
D O I
10.1002/chem.201002102
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A flowing future! A multistep, general flow chemistry protocol has been developed for the preparation of tyramine-based natural products. The process integrates room-temperature reactions with high-temperature Heck coupling reactions, where the heat has been supplied by microwave irradiation. As a proof of concept for 'scaling out' to attain larger quantities of the desired products, the four primary tyramine-based natural products were prepared on a gram scale using this synthetic protocol. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12797 / 12800
页数:4
相关论文
共 30 条
[1]   Multicomponent reactions to form heterocycles by microwave-assisted continuous flow organic synthesis [J].
Bremner, W. Stacy ;
Organ, Michael G. .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (01) :14-16
[2]   Aplysamine 6, an alkaloidal inhibitor of isoprenylcysteine carboxyl methyltransferase from the sponge Pseudoceratina sp. [J].
Buchanan, Malcolm S. ;
Carroll, Anthony R. ;
Fechner, Gregory A. ;
Boyle, Anthony ;
Simpson, Moana ;
Addepalli, Rama ;
Avery, Vicky M. ;
Hooper, John N. A. ;
Cheung, Tony ;
Chen, Huwei ;
Quinn, Ronald J. .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (06) :1066-1067
[3]   Amides and Benzenoids from Zanthoxylum ailanthoides with Inhibitory Activity on Superoxide Generation and Elastase Release by Neutrophils [J].
Chen, Jih-Jung ;
Chung, Ching-Yi ;
Hwang, Tsong-Long ;
Chen, Jinn-Fen .
JOURNAL OF NATURAL PRODUCTS, 2009, 72 (01) :107-111
[4]   Chemical and antiplatelet constituents from the stem of Zanthoxylum beecheyanum [J].
Cheng, MJ ;
Wu, CC ;
Tsai, AL ;
Chen, IS .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2004, 51 (5A) :1065-1072
[5]   A microcapillary system for simultaneous, parallel microwave-assisted synthesis [J].
Comer, E ;
Organ, MG .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (24) :7223-7227
[6]   A microreactor for microwave-assisted capillary (continuous flow) organic synthesis [J].
Comer, E ;
Organ, MG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :8160-8167
[7]  
García-Verdugo E, 2010, RSC GREEN CHEM SER, V5, P44
[8]   Fully Automated Continuous Flow Synthesis of Highly Functionalized Imidazo[1,2-a] Heterocycles [J].
Herath, Ananda ;
Dahl, Russell ;
Cosford, Nicholas D. P. .
ORGANIC LETTERS, 2010, 12 (03) :412-415
[9]   A flow-based synthesis of Imatinib: the API of Gleevec [J].
Hopkin, Mark D. ;
Baxendale, Ian R. ;
Ley, Steven V. .
CHEMICAL COMMUNICATIONS, 2010, 46 (14) :2450-2452
[10]   Inhibitory effect of trans-N-p-coumaroyl tryamine from the twigs of Celtis chinensis on the acetylcholinesterase [J].
Kim, DK ;
Lee, K .
ARCHIVES OF PHARMACAL RESEARCH, 2003, 26 (09) :735-738