Total synthesis of pyridovericin

被引:20
作者
Irlapati, NR
Adlington, RM
Conte, A
Pritchard, GJ
Marquez, R
Baldwin, JE
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
[2] Univ Loughborough, Dept Chem, Leicester 2LE11 3TU, Leics, England
[3] Univ Dundee, Sch Life Sci, Dundee DD1 4HN, Scotland
基金
英国工程与自然科学研究理事会;
关键词
pyridovericin; pyridomacrolidin; Suzuki coupling; metal-halogen exchange;
D O I
10.1016/j.tet.2004.07.035
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of the naturally occurring kinase inhibitor pyridovericin 1 is reported. A flexible and efficient synthesis has been accomplished in good yield from readily available 2,4-dihydroxypyridine. Pyridovericin is a key intermediate in our proposed biomimetic synthesis of pyridomacrolidin 2. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9307 / 9317
页数:11
相关论文
共 31 条
[11]  
IHARA M, 1994, HETEROCYCLES, V37, P289
[12]  
IHARA M, 1990, J CHEM SOC P1, V5, P1469
[13]   SYNTHESIS ON 1,4-DIAMINOCYCLITOL ANTIBIOTICS .3. SYNTHESIS OF 4-HYDROXYPURPUROSAMINE-B DERIVATIVES [J].
KANAI, K ;
SAKAMOTO, I ;
OGAWA, S ;
SUAMI, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (04) :1529-1531
[14]   Directed deprotonation-transmetalation as a route to substituted pyridines [J].
Karig, G ;
Spencer, JA ;
Gallagher, T .
ORGANIC LETTERS, 2001, 3 (06) :835-838
[15]  
LEETE E, 1975, TETRAHEDRON LETT, P4103
[16]   TYROSINE KINASE INHIBITION - AN APPROACH TO DRUG DEVELOPMENT [J].
LEVITZKI, A ;
GAZIT, A .
SCIENCE, 1995, 267 (5205) :1782-1788
[17]   Role of lactam vs. lactim tautomers in 2(1H)-pyridone catalysis of aromatic nucleophilic substitution [J].
Loppinet-Serani, A ;
Charbonnier, F ;
Rolando, C ;
Huc, I .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (04) :937-942
[18]  
MATSUMOTO M, 1976, TETRAHEDRON LETT, P3827
[19]   TENELLIN AND BASSIANIN, METABOLITES OF BEAUVERIA SPECIES - STRUCTURE ELUCIDATION WITH N-15-ENRICHED AND DOUBLY C-13-ENRICHED COMPOUNDS USING C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY [J].
MCINNES, AG ;
SMITH, DG ;
WAT, CK ;
VINING, LC ;
WRIGHT, JLC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (08) :281-282
[20]  
PADWA A, 1984, 1 3 DIPLOAR CYCLOADD, V2