PALLADIUM-CATALYZED CHEMOSELECTIVE REACTION OF ALLYLIC CARBONATE WITH NUCLEOSIDE BASES AND ITS APPLICATION FOR THE SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES - (-)-CARBOVIRS AND (+)-CARBOVIRS

被引：48

作者：

NOKAMI, J

MATSUURA, H

NAKASIMA, K

SHIBATA, S

机构：

来源：

CHEMISTRY LETTERS | 1994年 / 06期

关键词：

D O I：

10.1246/cl.1994.1071

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Palladium(0)-catalyzed reaction of 2-cyclopenten-1-yl methyl carbonate derivatives with nucleoside bases gave carbocyclic nucleosides chemo- and regioselectively under the neutral reaction conditions. The reaction was effectively used for the synthesis of (-)- and (+)-carbovir and its analogues.

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页码：1071 / 1074

页数：4

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共 29 条

[1] SHORT CONVERGENT ROUTE TO CHIRAL PYRIMIDINE ANALOGS OF 2'-DEOXY NEPLANOCIN-A [J].

BIGGADIKE, K ;

BORTHWICK, AD ;

EXALL, AM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (06) :458-459

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

BORTHWICK, AD ;

BIGGADIKE, K .

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

[3] PREPARATION OF NUCLEOTIDE MIMICS WITH POTENT INHIBITORY ACTIVITY AGAINST HIV REVERSE-TRANSCRIPTASE [J].

COE, DM ;

ORR, DC ;

ROBERTS, SM ;

STORER, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :3378-3379

[4] SYNTHESIS OF SOME MIMICS OF NUCLEOSIDE TRIPHOSPHATES [J].

COE, DM ;

HILPERT, H ;

NOBLE, SA ;

PEEL, MR ;

ROBERTS, SM ;

STORER, R .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (05) :312-314

[5] POTENTIAL USE OF CARBOCYCLIC NUCLEOSIDES FOR THE TREATMENT OF AIDS - CHEMOENZYMATIC SYNTHESES OF THE ENANTIOMERS OF CARBOVIR [J].

EVANS, CT ;

ROBERTS, SM ;

SHOBERU, KA ;

SUTHERLAND, AG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (05) :589-592

[6] PD(0)-CATALYZED ALLYLIC ALKYLATION IN THE SYNTHESIS OF (+/-)-CARBOVIR [J].

GUNDERSEN, LL ;

BENNECHE, T ;

UNDHEIM, K .

TETRAHEDRON LETTERS, 1992, 33 (08) :1085-1088

[7] TOTAL SYNTHESIS OF (-)-CARBOVIR [J].

JONES, MF ;

MYERS, PL ;

ROBERTSON, CA ;

STORER, R ;

WILLIAMSON, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (10) :2479-2484

[8] SYNTHESIS OF NUCLEOSIDES AND RELATED COMPOUNDS. 29. SYNTHESIS OF (1R,4S,5R)-9-(4,5-BISHYDROXY-METHYLCYCLOPENT-2-EN-1-YL)-9H-ADENINE [(-)-BCA] AND SELECTIVE-INHIBITION OF HUMAN-IMMUNODEFICIENCY-VIRUS [J].

KATAGIRI, N ;

TOYOTA, A ;

SHIRAISHI, T ;

SATO, H ;

KANEKO, C .

TETRAHEDRON LETTERS, 1992, 33 (24) :3507-3510

[9] A FACILE CHEMOENZYMATIC ROUTE TO OPTICALLY PURE BUILDING-BLOCKS FOR CYCLOPENTANOID NATURAL-PRODUCTS [J].

LAUMEN, K ;

SCHNEIDER, MP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (16) :1298-1299

[10] CONVERSION OF (-)-4-HYDROXY-2-OXABICYCLO[3.3.0]OCT-7-EN-3-ONE INTO THE ANTI-HIV AGENT CARBOVIR [J].

MACKEITH, RA ;

MCCAGUE, R ;

OLIVO, HF ;

PALMER, CF ;

ROBERTS, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (03) :313-314