EXPEDITIOUS SYNTHESIS OF AMINOCYCLOPENTITOLS FROM D-RIBOSE VIA INTRAMOLECULAR NITRONE CYCLOADDITION

被引：38

作者：

GALLOS, JK

GOGA, EG

KOUMBIS, AE

机构：

[1] Department of Chemistry, Aristotelian University of Thessaloniki

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 06期

关键词：

D O I：

10.1039/p19940000613

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 4alpha-aminocyclopentane-1alpha,2beta,3beta-triol (a key-intermediate in the preparation of carbocyclic nucleosides) and its N-substituted derivatives, has been achieved by the intramolecular nitrone cycloadditions of a gamma-unsaturated aldehyde, easily accessible from D-ribose, followed by reductive N-O bond cleavage in the resulting bicyclic oxazanes.

引用

收藏

页码：613 / 614

页数：2

相关论文

共 28 条

[1] (PHENYLTHIO)NITROMETHANE IN THE TOTAL SYNTHESIS OF POLYOXIN-C [J].

BARRETT, AGM ;

LEBOLD, SA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3853-3857

[2] 1,3-DIPOLAR CYCLOADDITION AS THE KEY REACTION IN THE SYNTHESIS OF POTENT RENIN INHIBITORS [J].

BENZ, G ;

HENNING, R ;

STASCH, JP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (12) :1702-1704

[3] CARBOCYCLIC COMPOUNDS FROM MONOSACCHARIDES .2. TRANSFORMATIONS IN THE MANNOSE SERIES [J].

BERNET, B ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1979, 62 (07) :2400-2410

[4] CARBOCYCLES FROM MONOSACCHARIDES .3. CONCERNING THE DIASTEREOSELECTIVE FORMATION OF CYCLOPENTANE DERIVATIVES - TRANSFORMATIONS IN THE GALACTOSE SERIES [J].

BERNET, B ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1979, 62 (07) :2411-2431

[5] SYNTHESIS OF CHIRAL CARBOCYCLIC NUCLEOSIDES [J].

BORTHWICK, AD ;

BIGGADIKE, K .

TETRAHEDRON, 1992, 48 (04) :571-623

[6] CONVERSION OF HYDROXYL-GROUPS INTO BROMO GROUPS IN CARBOHYDRATES WITH INVERSION OF CONFIGURATION [J].

CLASSON, B ;

GAREGG, PJ ;

SAMUELSSON, B .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (02) :339-343

[7] EXPEDITIOUS ENANTIOSELECTIVE SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES WITH ANTILEISHMANIAL ACTIVITY [J].

DASILVA, AD ;

COIMBRA, ES ;

FOURREY, JL ;

MACHADO, AS ;

ROBERTGERO, M .

TETRAHEDRON LETTERS, 1993, 34 (42) :6745-6748

[8] SYNTHESIS OF 1S,2R,3S,4R,5R-METHYL[2,3,4-TRIHYDROXY-5-(HYDROXYMETHYL)CYCLOPENTYL]AMINE - A POTENT ALPHA-MANNOSIDASE INHIBITOR [J].

FARR, RA ;

PEET, NP ;

KANG, MS .

TETRAHEDRON LETTERS, 1990, 31 (49) :7109-7112

[9] FUNCTIONALIZED CARBOCYCLES FROM CARBOHYDRATES .2. THE SYNTHESIS OF 3-OXA-2-AZABICYCLO[3.3.0]OCTANES - X-RAY CRYSTAL-STRUCTURE OF (1R,5S)-6-EXO,7-ENDO,8-EXO-TRIACETOXY-N-METHYL-4-ENDO-PHENYLTHIO-3-OXA-2-AZABICYCLO[3.3.0]OCTANE [J].

FERRIER, RJ ;

FURNEAUX, RH ;

PRASIT, P ;

TYLER, PC ;

BROWN, KL ;

GAINSFORD, GJ ;

DIEHL, JW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08) :1621-1628

[10] A GENERAL-ROUTE TO OPTICALLY PURE PROSTAGLANDINS FROM A D-GLUCOSE DERIVATIVE [J].

FERRIER, RJ ;

PRASIT, P .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (19) :983-985