Approaches to the fully functionalized DEF ring system of ristocetin A via highly selective ruthenium-promoted SNAr reaction

被引:36
作者
Pearson, AJ [1 ]
Heo, JN [1 ]
机构
[1] Case Western Reserve Univ, Dept Chem, Cleveland, OH 44106 USA
关键词
D O I
10.1021/ol000180h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
GRAPHICS Ruthenium-promoted intramolecular SNAr reaction has allowed the construction of the fully functionalized 16-membered DEF macrocycle 4 of ristocetin A that incorporates the required arylglycine and arylserine residues as the F and E ring, respectively.
引用
收藏
页码:2987 / 2990
页数:4
相关论文
共 33 条
[1]   Total synthesis of the teicoplanin aglycon [J].
Boger, DL ;
Kim, SH ;
Miyazaki, S ;
Strittmatter, H ;
Weng, JH ;
Mori, Y ;
Rogel, O ;
Castle, SL ;
McAtee, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7416-7417
[2]   Total synthesis of the vancomycin aglycon [J].
Boger, DL ;
Miyazaki, S ;
Kim, SH ;
Wu, JH ;
Castle, SL ;
Loiseleur, O ;
Jin, Q .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :10004-10011
[3]   AN EFFICIENT SYNTHESIS OF 3,5-DIHYDROXY-4-METHYLBENZOIC ACID [J].
BORCHARDT, RT ;
SINHABABU, AK .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24) :5021-5022
[4]  
Evans D.A., 1994, GLYCOPEPTIDE ANTIBIO, Vfirst, P63
[5]   Synthesis and conformational properties of the M(4-6)(5-7) bicyclic tetrapeptide common to the vancomycin antibiotics [J].
Evans, DA ;
Dinsmore, CJ ;
Ratz, AM ;
Evrard, DA ;
Barrow, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3417-3418
[6]   Approaches to the synthesis of the vancomycin antibiotics. Synthesis of orienticin C (bis-dechlorovancomycin) aglycon [J].
Evans, DA ;
Barrow, JC ;
Watson, PS ;
Ratz, AM ;
Dinsmore, CJ ;
Evrard, DA ;
DeVries, KM ;
Ellman, JA ;
Rychnovsky, SD ;
Lacour, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3419-3420
[7]  
Evans DA, 1998, ANGEW CHEM INT EDIT, V37, P2704, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2704::AID-ANIE2704>3.0.CO
[8]  
2-1
[9]  
Evans DA, 1998, ANGEW CHEM INT EDIT, V37, P2700, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO
[10]  
2-P