Studies directed towards the, synthesis of herbicidins. Model study based on late stage N-glycosylation

被引：9

作者：

Binch, HM

Gallagher, T

机构：

[1] School of Chemistry, University of Bristol, Bristol

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 05期

关键词：

NUCLEOSIDE ANTIBIOTICS; BOND;

D O I：

10.1039/p19960000401

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of nucleoside 6, via a regio- and stereoselective N-glycosylation of the undecose glycoside 4, is described. Nucleoside 6 is the first synthetic analogue of the herbicidin class of antibiotics to be reported and this model study also offers an insight into the scope and limitations associated with more general synthetic strategies based on a 'late stage' N-glycosylation.

引用

收藏

页码：401 / 402

页数：2

相关论文

共 20 条

[1] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF SELECTED ADENINE NUCLEOSIDES - STRUCTURAL CORRELATION AND CONFORMATION ABOUT THE GLYCOSIDIC BOND [J].

AKHREM, AA ;

MIKHAILOPULO, IA ;

ABRAMOV, AF .

ORGANIC MAGNETIC RESONANCE, 1979, 12 (04) :247-253

[2] HERBICIDIN-A AND HERBICIDIN-B, 2 NEW ANTIBIOTICS WITH HERBICIDAL ACTIVITY .1. PRODUCING ORGANISM AND BIOLOGICAL-ACTIVITIES [J].

ARAI, M ;

HANEISHI, T ;

KITAHARA, N ;

ENOKITA, R ;

KAWAKUBO, K ;

KONDO, Y .

JOURNAL OF ANTIBIOTICS, 1976, 29 (09) :863-869

[3] PUROMYCIN - SYNTHETIC STUDIES .2. THE POSITION OF GLYCOSIDATION ON THE 6-DIMETHYLAMINOPURINE MOIETY [J].

BAKER, BR ;

SCHAUB, RE ;

JOSEPH, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (04) :638-645

[4] SHORT SYNTHETIC ROUTE TO CONGENERS OF THE UNDECOSE ANTIBIOTIC HERBICIDIN [J].

BEARDER, JR ;

DEWIS, ML ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (03) :227-233

[5]

BEARDER JR, 1993, SYNLETT, P805

[6] REDUCTIVE CLEAVAGE AS A ROUTE TO CARBOHYDRATE ENOLATES - APPLICATIONS TO THE SYNTHESIS OF C-LINKED DISACCHARIDES [J].

BINCH, HM ;

GRIFFIN, AM ;

SCHWIDETZKY, S ;

RAMSAY, MVJ ;

GALLAGHER, T ;

LICHTENTHALER, FW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (09) :967-968

[7] THE SYNTHESIS OF 7-GLYCOSYLPURINES .1. SYNTHESES FROM PURINES [J].

BLACKBURN, GM ;

JOHNSON, AW .

JOURNAL OF THE CHEMICAL SOCIETY, 1960, (NOV) :4347-4358

[8] TOTAL SYNTHESIS OF UNDECULOFURANOSIDURONIC ACID-DERIVATIVES RELATED TO HERBICIDINS [J].

EMERY, F ;

VOGEL, P .

TETRAHEDRON LETTERS, 1993, 34 (26) :4209-4212

[9] SYNTHESIS OF UNDECULOFURANOSIDE DERIVATIVES OF THE HERBICIDINS AND OF ANALOGS [J].

EMERY, F ;

VOGEL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5843-5854

[10]

Garner P., 1988, STUD NAT PROD CHEM, V1, P397