A synthesis of racemic thalidomide

被引：16

作者：

Chang, MY

Chen, ST

Chang, NC

机构：

[1] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

[2] Acad Sinica, Inst Biol Chem, Taipei, Taiwan

来源：

SYNTHETIC COMMUNICATIONS | 2003年 / 33卷 / 08期

关键词：

thalidomide; formal [3+3] cycloaddition; glutarimides; alpha-sulfonylacetamide; ester;

D O I：

10.1081/SCC-120018698

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of racemic thalidomide is described using formal [3+3] cycloaddition strategy as the key step. The total yield of thalidomide was 30% in three steps from ester 2.

引用

页码：1375 / 1382

页数：8

共 19 条

[1]

CARLSTROM AS, 1989, SYNTHESIS-STUTTGART, P414

[2] 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

[3] STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF ANTICAPSIN AND RELATED-COMPOUNDS .2. DIELS-ALDER ADDITION OF N-ACYL DEHYDROALANINE ESTERS TO 1-TRIMETHYLSILYLOXYCYCLOHEXA-1,3-DIENE [J].

CROSSLEY, MJ ;

STAMFORD, AW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (09) :1695-1711

[4]

CROSSLEY MJ, 1998, J CHEM SOC P1, V6, P1113

[5]

Dawson N, 1998, CLIN CANCER RES, V4, P37

[6] An expeditious synthesis of cyclic imides [J].

Flaih, N ;

Pham-Huy, C ;

Galons, H .

TETRAHEDRON LETTERS, 1999, 40 (19) :3697-3698

[7] Synthesis of actiketal, a glutarimide antibiotic [J].

Kiyota, H ;

Shimizu, Y ;

Oritani, T .

TETRAHEDRON LETTERS, 2000, 41 (31) :5887-5890

[8] 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

[9] 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

[10] A concise two-step synthesis of thalidomide [J].

Muller, GW ;

Konnecke, WE ;

Smith, AM ;

Khetani, VD .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (02) :139-140

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