Carbocycles from carbohydrates via free radical cyclizations:: new synthetic approaches to glycomimetics

被引：95

作者：

Martínez-Grau, A

Marco-Contelles, J

机构：

[1] Fac Quim, Dept Quim Organ, Madrid 28040, Spain

[2] CSIC, Inst Quim Organ, E-28006 Madrid, Spain

来源：

CHEMICAL SOCIETY REVIEWS | 1998年 / 27卷 / 02期

关键词：

D O I：

10.1039/a827155z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Free radical cyclization of enantiomerically pure, acyclic presursors derived from carbohydrates is an excellent method for the synthesis of complex, densely functionalized chiral carbohydrate mimics ('glycomimetics'). The extent of the acyclic diastereoselection can be modulated and is closely associated with the structure, rigidity and conformational aspects of the radical precursors, General models for a rationale of the stereochemical outcome of the cyclizations are shown.

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页码：155 / 162

页数：8

相关论文

共 30 条

[1] STEREOCONTROLLED CONSTRUCTION OF 6 BULLET 5 BULLET 6 AND 5 BULLET 5 BULLET 6 RING-SYSTEMS BY RADICAL TANDEM CYCLIZATION [J].

ALBRECHT, U ;

WARTCHOW, R ;

HOFFMANN, HMR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (07) :910-913

[2] RADICAL CYCLIZATION OF OXIME ETHERS [J].

BARTLETT, PA ;

MCLAREN, KL ;

TING, PC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1633-1634

[3] SYNTHESIS OF A 1-ALPHA,25-DIHYDROXYVITAMIN-D3 A-RING MODEL BY AN ACYL RADICAL CYCLIZATION [J].

BATTY, D ;

CRICH, D ;

FORTT, SM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (18) :1366-1368

[4] REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS [J].

BECKWITH, ALJ .

TETRAHEDRON, 1981, 37 (18) :3073-3100

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

BORTHWICK, AD ;

BIGGADIKE, K .

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

[6] Stereoselective benzylic alpha-acylamino radical cyclisation: A model study for the Tacaman indole alkaloid skeleton [J].

Clauss, R ;

Hunter, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (01) :71-76

[7]

COLLINS P, 1995, MONOSACCHARIDES

[8]

DERUYTTERE X, 1992, SYNLETT, P51

[9] INHIBITORS OF THE BIOSYNTHESIS AND PROCESSING OF N-LINKED OLIGOSACCHARIDE CHAINS [J].

ELBEIN, AD .

ANNUAL REVIEW OF BIOCHEMISTRY, 1987, 56 :497-534

[10] SAMARIUM(II) IODIDE MEDIATED TRANSFORMATION OF CARBOHYDRATES TO CARBOCYCLES [J].

ENHOLM, EJ ;

TRIVELLAS, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6463-6465