Synthesis of 3-deoxy-3,3-difluoroshikimic acid and its 4-epimer from quinic acid

被引：31

作者：

Jiang, S

Singh, G ^{[1
]}

Boam, DJ

Coggins, JR

机构：

[1] Univ Sunderland, Dept Chem, Sunderland SR1 3SD, Durham, England

[2] Univ Glasgow, Dept Biochem & Mol Biol, Glasgow G12 8QQ, Lanark, Scotland

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 21期

关键词：

D O I：

10.1016/S0957-4166(99)00447-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

3-Deoxy-3,3-difluoroshikimic acid 2 and its 4-epimer 3 as new analogues of shikimic acid have been synthesised from quinic acid in overall yields of 30% and 12%, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4087 / 4090

页数：4

共 31 条

[1] The shikimate pathway .8. synthesis of (-)-3(R)-amino-4(R),5(R)-dihydroxy-1-cyclohexene-1-carboxylic acid: The 3(R)-amino analogue of (-)-shikimic acid [J].

Adams, H ;

Bailey, NA ;

Brettle, R ;

Cross, R ;

Frederickson, M ;

Haslam, E ;

MacBeath, FS ;

Davies, GM .

TETRAHEDRON, 1996, 52 (25) :8565-8580

[2] An efficient transformation of quinic acid to shikimic acid derivatives [J].

Alves, C ;

Barros, MT ;

Maycock, CD ;

Ventura, MR .

TETRAHEDRON, 1999, 55 (28) :8443-8456

[3] Synthesis of (-)-3(R)-amino-4(R),5(R)-dihydroxy-1-cyclohexene-1-carboxylic acid: The 3(R)-amino analogue of (-)-shikimic acid [J].

Brettle, R ;

Cross, R ;

Frederickson, M ;

Haslam, E ;

Davies, GM .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (03) :291-294

[4] The shikimate pathway .9. Halogenation at C-3 of the shikimate nucleus [J].

Brettle, R ;

Cross, R ;

Frederickson, M ;

Haslam, E ;

MacBeath, FS ;

Davies, GM .

TETRAHEDRON, 1996, 52 (31) :10547-10556

[5] Synthesis of (3R)- and (3S)-fluoro-(4R,5R)-dihydroxy-1-cyclohexene-1-carboxylic acids: The (3R)- and (3S)-fluoro analogues of (-)-shikimic acid [J].

Brettle, R ;

Cross, R ;

Frederickson, M ;

Haslam, E ;

MacBeath, FS ;

Davies, GM .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (11) :1275-1278

[6] SYNTHESIS OF (+/-)-HOMOGABACULINE AND (+/-)-HOMOSHIKIMIC ACID [J].

CAMPBELL, MM ;

MAHON, MF ;

SAINSBURY, M ;

SEARLE, PA ;

DAVIES, GM .

TETRAHEDRON LETTERS, 1991, 32 (07) :951-954

[7]

CAMPBELL MM, 1993, SYNTHESIS-STUTTGART, P179

[8] Enantiospecific synthesis of cyanocyclitols and (6R)-6-hydroxyshikimic acid from benzonitrile [J].

Carless, HAJ ;

Dove, Y .

TETRAHEDRON-ASYMMETRY, 1996, 7 (03) :649-652

[9] Synthesis of 2-bromo- and 2-fluoro-3-dehydroshikimic acids and 2-bromo- and 2-fluoroshikimic acids using synthetic and enzymatic approaches [J].

González-Bello, C ;

Manthey, MK ;

Harris, JH ;

Hawkins, AR ;

Coggins, JR ;

Abell, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1591-1597

[10]

Grossbard E, 1985, HERBICIDE GLYPHOSATE

← 1 2 3 4 →