Carbocyclic ring closure of hex-5-enopyranosides and pent-4-enofuranosides: a nitrile oxide approach

被引：34

作者：

Gallos, JK ^{[1
]}

Koftis, TV ^{[1
]}

机构：

[1] Aristotelian Univ Salonika, Dept Chem, GR-54006 Salonika, Greece

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 04期

关键词：

D O I：

10.1039/b007654f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrile oxide cycloadditions to protected enopyrano(furano)sides derived from D-glucose and D-ribose afford spiro-isoxazolines in good yield and high diastereoselectivity, which upon Raney Nickel hydrogenation in MeOH-AcOH (6:1) undergo N-O bond cleavage followed by spontaneous aldol-like condensation to give good yields of hydroxylated six- and five-membered cyclic enaminones as the main products.

引用

页码：415 / 423

页数：9

共 60 条

[1] PALLADIUM(II) PROMOTED CARBOCYCLIZATION OF AMINODEOXYHEX-5-ENOPYRANOSIDES [J].

ADAM, S .

TETRAHEDRON LETTERS, 1988, 29 (50) :6589-6592

[2] SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].

AGROFOGLIO, L ;

SUHAS, E ;

FARESE, A ;

CONDOM, R ;

CHALLAND, SR ;

EARL, RA ;

GUEDJ, R .

TETRAHEDRON, 1994, 50 (36) :10611-10670

[3]

AKHREM AA, 1976, TETRAHEDRON LETT, P3983

[4] Probing the specificity of aminoglycoside ribosomal RNA interactions with designed synthetic analogs [J].

Alper, PB ;

Hendrix, M ;

Sears, P ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (09) :1965-1978

[5] CONVENIENT PROCEDURE FOR THE REDUCTION OF BETA-ENAMINO KETONES - SYNTHESIS OF GAMMA-AMINO ALCOHOLS AND TETRAHYDRO-1,3-OXAZINES [J].

BARTOLI, G ;

CIMARELLI, C ;

PALMIERI, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (05) :537-543

[6]

BARTON DHR, 1990, TETRAHEDRON, V46, P215

[7] Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues [J].

Berecibar, A ;

Grandjean, C ;

Siriwardena, A .

CHEMICAL REVIEWS, 1999, 99 (03) :779-844

[8] FUNCTIONALIZED CARBOCYCLES FROM CARBOHYDRATES .8. UNSATURATED CARBOHYDRATES .28. OBSERVATIONS ON THE CONVERSION OF 6-DEOXYHEX-5-ENOPYRANOSYL COMPOUNDS INTO 2-DEOXYINOSOSE DERIVATIVES [J].

BLATTNER, R ;

FERRIER, RJ ;

HAINES, SR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2413-2416

[9] CYCLOADDITION OF NITRILE OXIDES TO HOMOCHIRAL VINYL ETHERS [J].

BOA, AN ;

BOOTH, SE ;

DAWKINS, DA ;

JENKINS, PR ;

FAWCETT, J ;

RUSSELL, DR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (12) :1277-1278

[10] CYCLOADDITION OF NITRILE OXIDES TO HOMOCHIRAL VINYL ETHERS [J].

BOA, AN ;

DAWKINS, DA ;

HERGUETA, AR ;

JENKINS, PR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (08) :953-960

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