2-azabicyclo[2.2.1]hept-5-en-3-one epoxide:: A versatile intermediate for the synthesis of cyclopentyl carbocyclic 2-deoxy-, 3-deoxy- & ara-ribonucleoside analogues.

被引：24

作者：

Domínguez, BM ^{[1
]}

Cullis, PM ^{[1
]}

机构：

[1] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(99)01113-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5,6-Epoxy-exo-2-azabicyclo[2.2.1]heptan-3-one has been used as a versatile intermediate in the synthesis of 2-deoxy-, 3-deoxy- and ara- cyclopentyl carbocyclic nucleosides. An efficient, short synthesis of the (+) carbocyclic thymidine 13 is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5783 / 5786

页数：4

共 13 条

[1] SYNTHESIS OF 3 NEW CARBOCYCLIC ANALOGS OF 3'-DEOXY PURINE RIBONUCLEOSIDES [J].

AGROFOGLIO, L ;

CONDOM, R ;

GUEDJ, R ;

CHALLAND, SR ;

SELWAY, J .

NUCLEOSIDES & NUCLEOTIDES, 1994, 13 (05) :1147-1160

[2] STEREOSPECIFIC SYNTHESIS AND ANTIVIRAL PROPERTIES OF DIFFERENT ENANTIOMERICALLY PURE CARBOCYCLIC 2'-DEOXYRIBONUCLEOSIDE ANALOGS DERIVED FROM COMMON CHIRAL POOLS - (+)-(1R,5S)-2-OXABICYCLO[3.3.0]OCT-6-EN-3-ONE AND (-)-(1S,5R)-2-OXABICYCLO[3.3.0]OCT-6-EN-3-ONE [J].

BERES, J ;

SAGI, G ;

TOMOSKOZI, I ;

GRUBER, L ;

BAITZGACS, E ;

OTVOS, L ;

DECLERCQ, E .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) :1353-1360

[3] IMPROVED PROCEDURES FOR THE PREPARATION OF (+)-(1R,2S,4R)-4-AMINO-2-HYDROXY-1-HYDROXYMETHYL CYCLOPENTANE [J].

BRAY, BL ;

DOLAN, SC ;

HALTER, B ;

LACKEY, JW ;

SCHILLING, MB ;

TAPOLCZAY, DJ .

TETRAHEDRON LETTERS, 1995, 36 (25) :4483-4486

[4] CHIROSPECIFIC SYNTHESES OF PRECURSORS OF CYCLOPENTANE AND CYCLOPENTENE CARBOCYCLIC NUCLEOSIDES BY [3+3]-COUPLING AND TRANSANNULAR ALKYLATION [J].

CAMPBELL, JA ;

LEE, WK ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (14) :4602-4616

[5] THE POTENTIAL OF CARBOCYCLIC NUCLEOSIDES FOR THE TREATMENT OF AIDS - SYNTHESIS OF SOME DIPHOSPHORYLPHOSPHONATES POSSESSING POTENT ACTIVITY AGAINST HIV-CODED REVERSE-TRANSCRIPTASE [J].

COE, DM ;

ROBERTS, SM ;

STORER, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (20) :2695-2704

[6] New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides [J].

Crimmins, MT .

TETRAHEDRON, 1998, 54 (32) :9229-9272

[7] SYNTHESIS OF NUCLEOSIDES AND THEIR RELATED-COMPOUNDS .13. STEREOSPECIFIC SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES FROM 2-AZABICYCLO[2.2.1]HEPTAN-3-ONES VIA SODIUM-BOROHYDRIDE MEDIATED CARBON-NITROGEN BOND-CLEAVAGE [J].

KATAGIRI, N ;

MUTO, M ;

KANEKO, C .

TETRAHEDRON LETTERS, 1989, 30 (13) :1645-1648

[8] A highly efficient synthesis of the antiviral agent (+)-cyclaradine involving the regioselective cleavage of epoxide by neighboring participation [J].

Katagiri, N ;

Matsuhashi, Y ;

Kokufuda, H ;

Takebayashi, M ;

Kaneko, C .

TETRAHEDRON LETTERS, 1997, 38 (11) :1961-1964

[9]

LEGRAVEREND M, 1989, J HETEROCYCLIC CHEM, V26, P1881

[10] Methylated derivative of 5'-noraristeromycin [J].

Seley, KL ;

Shneller, SW ;

DeClercq, E .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5645-5646

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