Synthesis of carbocyclic C-nucleosides containing nonnatural pyrimidine bases

被引：16

作者：

Hildbrand, S ^{[1
]}

Leumann, C ^{[1
]}

Scheffold, R ^{[1
]}

机构：

[1] UNIV BERN,INST ORGAN CHEM,CH-3012 BERN,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1996年 / 79卷 / 03期

关键词：

D O I：

10.1002/hlca.19960790312

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of new carbocyclic C-nucleosides with a cis-4'-(hydroxymethyl)cyclopent-2'-enyl sugar moiety and unnatural pyrimidine bases (2-6) were synthesized in racemic form in two steps starting from the easily accessible cyclic carbonate 1.

引用

页码：702 / 709

页数：8

共 17 条

[1] 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

[2] MODIFIED PRINS REACTION APPLICABLE TO CONJUGATED DIENES [J].

BAJOREK, JJS ;

BATTAGLI.R ;

PRATT, G ;

SUTHERLA.JK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (11) :1243-1245

[3] ALLYLIC SUBSTITUTION USING HETEROGENEOUS PALLADIUM CATALYSTS [J].

BERGBREITER, DE ;

CHEN, B .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (21) :1238-1239

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

BORTHWICK, AD ;

BIGGADIKE, K .

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

[5]

BROWN DJ, 1994, CHEM HETEROCYCLIC CO, V52, P236

[6] SYNTHESIS OF CARBOCYCLIC C-NUCLEOSIDE ANALOGS FROM 8,9,10-TRINORBORN-5-EN-2-OL [J].

COOKSON, RC ;

DUDFIELD, PJ ;

SCOPES, DIC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (03) :393-398

[7] PALLADIUM-ASSISTED ROUTE TO CARBOCYCLIC NUCLEOSIDES - A FORMAL SYNTHESIS OF (+/-)-ARISTEROMYCIN [J].

DEARDORFF, DR ;

SHULMAN, MJ ;

SHEPPECK, JE .

TETRAHEDRON LETTERS, 1989, 30 (48) :6625-6628

[8] C-NUCLEOSIDES .2. PREPARATION OF 2-[(1R,2S,3R,4R)-2,3-DIHYDROXY-4-(HYDROXYMETHYL)CYCLOPENTYL]THIAZOLE-4-CARBOXAMIDE (CARBOCYCLIC TIAZOFURIN) AND ITS ANTIPODE [J].

DISHINGTON, AP ;

HUMBER, DC ;

STOODLEY, RJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (01) :57-65

[9] A SHORT SYNTHESIS OF (-)-CARBOVIR [J].

HILDBRAND, S ;

TROXLER, T ;

SCHEFFOLD, R .

HELVETICA CHIMICA ACTA, 1994, 77 (05) :1236-1240

[10] A NEW METHOD FOR THE HIGHLY STEREOSELECTIVE SYNTHESIS OF NUCLEOSIDES - CREATION OF NEW DIENOPHILES AND USE OF REDUCTIVE RETROGRADE ALDOL REACTION [J].

KATAGIRI, N .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1989, 47 (08) :707-721

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