ENANTIOSPECIFIC SYNTHESIS OF (-)-5-EPI-SHIKIMIC ACID AND A NEW ROUTE TO (-)-SHIKIMIC ACID

被引：32

作者：

JIANG, SD

MEKKI, B

SINGH, G

WIGHTMAN, RH

机构：

[1] UNIV TEESIDE,SCH SCI & TECHNOL,MIDDLESBROUGH TS1 3BA,CLEVELAND,ENGLAND

[2] HERIOT WATT UNIV,DEPT CHEM,EDINBURGH EH14 4AS,MIDLOTHIAN,SCOTLAND

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(00)73536-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-Shikimic acid (1) and (-)-5-epi-shikimic acid (2) have each been prepared enantiospecifically and with high diastereoselectivity from D-ribose.

引用

页码：5505 / 5508

页数：4

共 19 条

[1]

[Anonymous], 1993, SHIKIMIC ACID METABO

[2] STEREOSPECIFIC SYNTHESIS OF OPTICALLY PURE QUINIC ACID AND SHIKIMIC ACID FROM D-ARABINOSE [J].

BESTMANN, HJ ;

HEID, HA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (05) :336-&

[3] ENATIOSPECIFIC SYNTHESIS OF (+)-RETRONECINE, (+)-CROTONECINE, AND RELATED ALKALOIDS [J].

BUCHANAN, JG ;

JIGAJINNI, VB ;

SINGH, G ;

WIGHTMAN, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (11) :2377-2384

[4]

CAMPBELL MM, 1993, SYNTHESIS-STUTTGART, P179

[5] BRIEF SYNTHESES OF (+/-)-METHYL SHIKIMATE, (+/-)-METHYL EPISHIKIMATE AND STRUCTURAL VARIANTS [J].

CAMPBELL, MM ;

KAYE, AD ;

SAINSBURY, M ;

YAVARZADEH, R .

TETRAHEDRON, 1984, 40 (13) :2461-2470

[6] SELECTIVE OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS WITH SODIUM-CHLORITE HYDROGEN-PEROXIDE [J].

DALCANALE, E ;

MONTANARI, F .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :567-569

[7] THE CONVERSION OF CARBOHYDRATE-DERIVATIVES INTO FUNCTIONALIZED CYCLOHEXANES AND CYCLOPENTANES [J].

FERRIER, RJ ;

MIDDLETON, S .

CHEMICAL REVIEWS, 1993, 93 (08) :2779-2831

[8] ENANTIOSPECIFIC SYNTHESIS OF SHIKIMIC ACID FROM D-MANNOSE - FORMATION OF A CHIRAL CYCLOHEXENE BY INTRAMOLECULAR OLEFINATION OF A CARBOHYDRATE-DERIVED INTERMEDIATE [J].

FLEET, GWJ ;

SHING, TKM ;

WARR, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :905-908

[9]

MCCULLOUGH KJ, UNPUB STRUCTURE 8 CO

[10] REACTIONS OF 2,3-O-ISOPROPYLIDENE DERIVATIVES OF FURANOSE SUGARS WITH ORGANOMAGNESIUM AND ORGANOLITHIUM NUCLEOPHILES [J].

MEKKI, B ;

SINGH, G ;

WIGHTMAN, RH .

TETRAHEDRON LETTERS, 1991, 32 (38) :5143-5146

← 1 2 →