High-Yielding Synthesis of the Anti-Influenza Neuramidase Inhibitor (-)-Oseltamivir by Three "One-Pot" Operations

被引:342
作者
Ishikawa, Hayato [1 ]
Suzuki, Takaki [1 ]
Hayashi, Yujiro [1 ,2 ]
机构
[1] Tokyo Univ Sci, Dept Ind Engn, Fac Engn, Shinjyuku Ku, Tokyo 1628601, Japan
[2] Tokyo Univ Sci, Sci & Technol Res Inst, Tokyo 1628601, Japan
关键词
antiviral agents; domino reactions; organocatalysis; oseltamivir; Tamiflu; DIPHENYLPROLINOL SILYL ETHER; ASYMMETRIC MICHAEL REACTION; OSELTAMIVIR; TAMIFLU; PHOSPHATE; CATALYST; ALDEHYDES; FUNCTIONALIZATION; ORGANOCATALYSIS; ACETALDEHYDE;
D O I
10.1002/anie.200804883
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Taking shortcuts: A remarkably short and high-yielding asymmetric total synthesis of (-)-oseltamivir takes advantage of organocatalysis and single-pot domino operations. The target, known as the drug Tamiflu, is prepared efficiently in a short time, and also its derivatives can be synthesized effectively. © 2009 Wiley-VCH Verleg GmbH & Co. KGaA.
引用
收藏
页码:1304 / 1307
页数:4
相关论文
共 62 条
[11]   In the golden age of organocatalysis [J].
Dalko, PI ;
Moisan, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175
[12]  
Dondoni A., 2008, Angew. Chem, V120, P4716, DOI DOI 10.1002/ANGE.200704684
[13]   Asymmetric organocatalysis: From infancy to adolescence [J].
Dondoni, Alessandro ;
Massi, Alessandro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4638-4660
[14]   Control of four stereocentres in a triple cascade organocatalytic reaction [J].
Enders, Dieter ;
Hüettl, Matthias R. M. ;
Grondal, Christoph ;
Raabe, Gerhard .
NATURE, 2006, 441 (7095) :861-863
[15]   Tamiflu: The supply problem [J].
Farina, Vittorio ;
Brown, Jack D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (44) :7330-7334
[16]   Industrial synthesis of the key precursor in the synthesis of the anti-influenza drug oseltamivir phosphate (Ro 64-0796/002, GS-4104-02):: Ethyl (3R,4S,5S)-4,5-epoxy-3-(1-ethyl-propoxy)-cyclohex-1-ene-1-carboxylate [J].
Federspiel, M ;
Fischer, R ;
Hennig, M ;
Mair, HJ ;
Oberhauser, T ;
Rimmler, G ;
Albiez, T ;
Bruhin, J ;
Estermann, H ;
Gandert, C ;
Göckel, V ;
Götzö, S ;
Hoffmann, U ;
Huber, G ;
Janatsch, G ;
Lauper, S ;
Röckel-Stäbler, O ;
Trussardi, R ;
Zwahlen, AG .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (04) :266-274
[17]   Organocatalytic enantioselective one-pot synthesis and application of substituted 1,4-dihydropyridines - Hantzsch Ester analogues [J].
Franke, Patrick T. ;
Johansen, Rasmus L. ;
Bertelsen, Soren ;
Jorgensen, Karl Anker .
CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (02) :216-224
[18]   De novo synthesis of Tamiflu via a catalytic asymmetric ring-opening of meso-aziridines with TMSN3 [J].
Fukuta, Yuhei ;
Mita, Tsuyoshi ;
Fukuda, Nobuhisa ;
Kanai, Motomu ;
Shibasaki, Masakatsu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) :6312-6313
[19]   Enantioselective organocatalysis [J].
Gaunt, Matthew J. ;
Johansson, Carin C. C. ;
McNally, Andy ;
Vo, Ngoc T. .
DRUG DISCOVERY TODAY, 2007, 12 (1-2) :8-27
[20]  
Gotoh H., 2006, ANGEW CHEM, V118, P7007