An expedient asymmetric synthesis of platencin

被引:74
作者
Nicolaou, K. C. [1 ]
Toh, Qiao-Yan [1 ]
Chen, David Y. K. [1 ]
机构
[1] ASTAR, ICES, Chem Synth Lab Biopolis, Singapore 138667, Singapore
关键词
D O I
10.1021/ja804588r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A shod and efficient synthesis of enone 3, a key intermediate in the total synthesis of platencin (2), based on an intramolecular Diels-Alder reaction is described.
引用
收藏
页码:11292 / +
页数:3
相关论文
共 43 条
[1]   INHA, A GENE ENCODING A TARGET FOR ISONIAZID AND ETHIONAMIDE IN MYCOBACTERIUM-TUBERCULOSIS [J].
BANERJEE, A ;
DUBNAU, E ;
QUEMARD, A ;
BALASUBRAMANIAN, V ;
UM, KS ;
WILSON, T ;
COLLINS, D ;
DELISLE, G ;
JACOBS, WR .
SCIENCE, 1994, 263 (5144) :227-230
[2]  
BLADOCK C, 1999, SCIENCE, V274, P2107
[3]   Bacterial fatty acid biosynthesis: Targets for antibacterial drug discovery [J].
Campbell, JW ;
Cronan, JE .
ANNUAL REVIEW OF MICROBIOLOGY, 2001, 55 :305-332
[4]   Diastereoselective intramolecular Diels-Alder reactions of masked o-benzoquinones:: a short entry to highly functionalized tricyclic [m.2.2.0] ring systems [J].
Chen, YK ;
Peddinti, RK ;
Liao, CC .
CHEMICAL COMMUNICATIONS, 2001, (15) :1340-1341
[5]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO
[6]  
2-Z
[7]   Identification and characterization of the first class of potent bacterial acetyl-CoA carboxylase inhibitors with antibacterial activity [J].
Freiberg, C ;
Brunner, NA ;
Schiffer, G ;
Lampe, T ;
Pohlmann, J ;
Brands, M ;
Raabe, M ;
Häbich, D ;
Ziegelbauer, K .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (25) :26066-26073
[8]   Total synthesis of (±)-platencin [J].
Hayashida, Joji ;
Rawal, Viresh H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (23) :4373-4376
[9]  
Heath Richard J, 2004, Curr Opin Investig Drugs, V5, P146
[10]   Broad spectrum antimicrobial biocides target the FabI component of fatty acid synthesis [J].
Heath, RJ ;
Yu, YT ;
Shapiro, MA ;
Olson, E ;
Rock, CO .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1998, 273 (46) :30316-30320