Synthesis of polyhydroxylated pyrano-pyrrole derivatives from carbohydrate precursors

被引：29

作者：

Naud, Sebastien

Pipelier, Muriel

Viault, Guillaume

Adjou, Ane

Huet, Francois

Legoupy, Stephanie

Aubertin, Anne-Marie

Evain, Michel

Dubreuil, Didier

机构：

[1] Univ Nantes, CNRS, Organ Synth Lab, UMR 6513,Fac Sci & Tech, F-44322 Nantes 3, France

[2] Univ Maine, CNRS, Synth Organ Lab,Fac Sci & Tech, UCO2M,UMR 6011, F-72085 Le Mans 9, France

[3] Univ Strasbourg, INSERM U544, Fac Med, Inst Virol, F-67000 Strasbourg, France

[4] Univ Nantes, CNRS, Inst Mat Jean Rouxel, UMR 6502,Fac Sci & Tech, F-44322 Nantes 3, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 20期

关键词：

cycloaddition; ring contraction; pyridazine; pyrrole; alpha-pyrone; carbohydrates;

D O I：

10.1002/ejoc.200700102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The efficient synthesis of novel polyhydroxy-tetrahydropyrano-pyrroles from acetylenic carbohydrate precursors in three to four steps is described. The methodology involves, as key steps, the ring contraction of pyridazine intermediates obtained by an inverse-demand Diels-Alder reaction and subsequent intramolecular lactonization. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

收藏

页码：3296 / 3310

页数：15

相关论文

共 33 条

[1] GONIOTRIOL FROM GONIOTHALAMUS-GIGANTEUS [J].

ALKOFAHI, A ;

MA, WW ;

MCKENZIE, AT ;

BYRN, SR ;

MCLAUGHLIN, JL .

JOURNAL OF NATURAL PRODUCTS, 1989, 52 (06) :1371-1373

[2] CYTOTOXICITY OF HYMENOCALLIS-EXPANSA ALKALOIDS [J].

ANTOUN, MD ;

MENDOZA, NT ;

RIOS, YR ;

PROCTOR, GR ;

WICKRAMARATNE, DBM ;

PEZZUTO, JM ;

KINGHORN, AD .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (08) :1423-1425

[3] 2,3,5-TRI-O-BENZYL-D-RIBOSYL AND -L-ARABINOSYL BROMIDES [J].

BARKER, R ;

FLETCHER, HG .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (11) :4605-&

[4]

Boger D. L., 1992, Org. Synth, V70, P79

[5] A DETAILED, CONVENIENT PREPARATION OF DIMETHYL "1,2,4,5-TETRAZINE-3,6-DICARBOXYLATE [J].

BOGER, DL ;

COLEMAN, RS ;

PANEK, JS ;

HUBER, FX ;

SAUER, J .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5377-5379

[6] THERMAL CYCLOADDITION OF DIMETHYL "1,2,4,5-TETRAZINE-3,6-DICARBOXYLATE WITH ELECTRON-RICH OLEFINS - 1,2-DIAZINE AND PYRROLE INTRODUCTION - PREPARATION OF OCTAMETHYLPORPHIN (OMP) [J].

BOGER, DL ;

COLEMAN, RS ;

PANEK, JS ;

YOHANNES, D .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23) :4405-4409

[7] C-NUCLEOSIDE STUDIES .1. SYNTHESIS OF [2,3,5-TRI-ORTHO-BENZYL-ALPHA(AND BETA-)-D-RIBOFURANOSYL]ETHYNE [J].

BUCHANAN, JG ;

EDGAR, AR ;

POWER, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (16) :1943-1949

[8] Antiparasite and antimycobacterial activity of passifloricin analogues [J].

Cardona, W ;

Quiñones, W ;

Robledo, S ;

Vélez, ID ;

Murga, J ;

García-Fortanet, J ;

Carda, M ;

Cardona, D ;

Echeverri, F .

TETRAHEDRON, 2006, 62 (17) :4086-4092

[9] SYNTHESIS AND REACTIONS OF AN (ALPHA-D-GLUCOPYRANOSYL)PHENYLACETYLENE [J].

DESIRE, J ;

VEYRIERES, A .

CARBOHYDRATE RESEARCH, 1995, 268 (02) :177-186

[10] Synthesis of α- and β-glycosyl asparagine ethylene isosteres (C-glycosyl asparagines) via sugar acetylenes and Garner aldehyde coupling [J].

Dondoni, A ;

Mariotti, G ;

Marra, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4475-4486

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