Total synthesis of ustiloxin D

被引:63
作者
Cao, B [1 ]
Park, H [1 ]
Joullié, MM [1 ]
机构
[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ja017277z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The total synthesis of ustiloxin D, a highly potent inhibitor of microtubule assembly, has been achieved. Notable features are the use of nucleophilic aromatic substitution (SNAr) for the construction of a chiral tertiary alkyl-aryl ether linkage, Sharpless asymmetric aminohydroxylation for the formation of the β-hydroxytyrosine moiety, macrolactamization, and regioselective methylation. Copyright © 2002 American Chemical Society.
引用
收藏
页码:520 / 521
页数:2
相关论文
共 35 条
[1]   ENANTIOSPECIFIC AND DIASTEREOSELECTIVE SYNTHESIS OF 4,4-DISUBSTITUTED-3-AMINO-2-AZETIDINONES, STARTING FROM D-SERINE [J].
AGENO, G ;
BANFI, L ;
CASCIO, G ;
GUANTI, G ;
MANGHISI, E ;
RIVA, R ;
ROCCA, V .
TETRAHEDRON, 1995, 51 (29) :8121-8134
[2]  
BARTON DHR, 1982, J CHEM SOC P1, V7, P1541
[3]  
BITTNER S, 1975, CHEM IND-LONDON, P281
[4]   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
[5]   Synthesis of conjugated spiropyran dyes via palladium-catalyzed coupling reaction [J].
Cho, YJ ;
Rho, KY ;
Keum, SR ;
Kim, SH ;
Yoon, CM .
SYNTHETIC COMMUNICATIONS, 1999, 29 (12) :2061-2068
[6]   THE CONVERSION OF PHENOLS TO PRIMARY AND SECONDARY AROMATIC-AMINES VIA A SMILES REARRANGEMENT [J].
COUTTS, IGC ;
SOUTHCOTT, MR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :767-771
[7]  
Hamel E, 1996, MED RES REV, V16, P207, DOI 10.1002/(SICI)1098-1128(199603)16:2<207::AID-MED4>3.3.CO
[8]  
2-I
[9]   TOTAL SYNTHESIS OF (-)-NUMMULARINE-F [J].
HEFFNER, RJ ;
JIANG, JJ ;
JOULLIE, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10181-10189
[10]   Towards a total synthesis of ustiloxins A & B. Stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline [J].
Hutton, CA ;
White, JM .
TETRAHEDRON LETTERS, 1997, 38 (09) :1643-1646