Synthesis of vigabatrin®

被引：7

作者：

Chang, Meng-Yang ^{[1
]}

Lin, Chun-Yu

Ong, Chi-Wi

机构：

[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan

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

来源：

HETEROCYCLES | 2006年 / 68卷 / 10期

关键词：

D O I：

10.3987/COM-06-10837

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of vigabatrin (R) has been achieved from trans-(2S,4R)-4-hydroxyproline via the key regioselective Baeyer-Villiger lactonization reaction.

引用

页码：2031 / +

页数：7

共 47 条

[1] Enantioselective synthesis of (S)-Vigabatrin(R) [J].

Alcon, M ;

Poch, M ;

Moyano, A ;

Pericas, MA ;

Riera, A .

TETRAHEDRON-ASYMMETRY, 1997, 8 (17) :2967-2974

[2] Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity [J].

Anderson, CE ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12412-12413

[3] Phase-transfer-catalyzed asymmetric Michael reaction using newly-prepared chiral quaternary ammonium salts derived from L-tartrate [J].

Arai, S ;

Tsuji, R ;

Nishida, A .

TETRAHEDRON LETTERS, 2002, 43 (52) :9535-9537

[4] A novel one-pot synthesis of some new interesting pyrrole derivatives [J].

Azizian, J ;

Karimi, AR ;

Kazemizadeh, Z ;

Mohammadi, AA ;

Mohammadizadeh, MR .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04) :1471-1473

[5]

BRESLIN HJ, 1995, J MED CHEM, V38, P771, DOI 10.1021/jm00005a005

[6] Stereoselective synthesis of β-substituted aspartic acids via tetrahydro-1,3-oxazin-6-ones [J].

Burtin, G ;

Corringer, PJ ;

Hitchcock, PB ;

Young, DW .

TETRAHEDRON LETTERS, 1999, 40 (22) :4275-4278

[7] Tetrahydro-1,3-oxazin-6-ones as templates for the stereoselective synthesis of β-substituted L-aspartic acids [J].

Burtin, G ;

Corringer, PJ ;

Young, DW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (20) :3451-3459

[8] VIGABATRIN SYNTHESIS BY THERMAL REARRANGEMENTS [J].

CASARA, P .

TETRAHEDRON LETTERS, 1994, 35 (19) :3049-3050

[9] Regioselective Baeyer-Villiger lactonization of 2-substituted pyrrolidin-4-one. Synthesis of statine [J].

Chang, Meng-Yang ;

Kung, Yung-Hua ;

Chen, Shui-Tein .

TETRAHEDRON LETTERS, 2006, 47 (28) :4865-4870

[10] Synthesis of streptorubin B core [J].

Chang, MY ;

Pai, CL ;

Chen, HP .

TETRAHEDRON LETTERS, 2005, 46 (45) :7705-7709

← 1 2 3 4 5 →