A synthesis of thalidomide

被引:12
作者
Chang, MY
Chang, CH
Chen, ST [1 ]
Chang, NC
机构
[1] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan
[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan
关键词
glutarimides; thalidomide; formal [3+3] cycloaddition reaction; phthaloylation;
D O I
10.1002/jccs.200200060
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A synthesis of racemic thalidomide (1) was described and the important formal [3 +3] cycloaddition strategy was a key step. The total yield of thalidomide (1) was 18% in five steps from known 3.
引用
收藏
页码:383 / 385
页数:3
相关论文
共 16 条
[1]  
AMATO RD, Patent No. 940085
[2]  
BLASCHKE G, 1979, ARZNEIMITTEL-FORSCH, V29-2, P1640
[3]   An efficient synthesis of N-benzyl-3-sulfonyl glutarimides.: Formal synthesis of the aromatase inhibitor AG-1 [J].
Chang, MY ;
Chang, BR ;
Tai, HM ;
Chang, NC .
TETRAHEDRON LETTERS, 2000, 41 (52) :10273-10276
[4]  
Dawson N, 1998, CLIN CANCER RES, V4, P37
[5]   PREPARATION OF ENANTIOMERICALLY PURE PROTECTED 4-OXO-ALPHA-AMINO ACIDS AND 3-ARYL-ALPHA-AMINO ACIDS FROM SERINE [J].
JACKSON, RFW ;
WISHART, N ;
WOOD, A ;
JAMES, K ;
WYTHES, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3397-3404
[6]   Synthesis of actiketal, a glutarimide antibiotic [J].
Kiyota, H ;
Shimizu, Y ;
Oritani, T .
TETRAHEDRON LETTERS, 2000, 41 (31) :5887-5890
[7]   THALIDOMIDE INHIBITS THE REPLICATION OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 [J].
MAKONKAWKEYOON, S ;
LIMSONPOBRE, RNR ;
MOREIRA, AL ;
SCHAUF, V ;
KAPLAN, G .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (13) :5974-5978
[8]   Thalidomide and thalidomide analogs reduce HIV type 1 replication in human macrophages in vitro [J].
Moreira, AL ;
Corral, LG ;
Ye, WG ;
Johnson, B ;
Stirling, D ;
Muller, GW ;
Freedman, VH ;
Kaplan, G .
AIDS RESEARCH AND HUMAN RETROVIRUSES, 1997, 13 (10) :857-863
[9]  
NAZAR F, 1999, TETRAHEDRON LETT, V40, P3697
[10]  
NISHIMURA K, 1994, CHEM PHARM BULL, V42, P1157