First synthesis of 2′,3′-epimino-carbocydic nucleosides

被引:19
作者
Ishikura, M [1 ]
Murakami, A [1 ]
Katagiri, N [1 ]
机构
[1] Hlth Sci Univ Hokkaido, Fac Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan
关键词
D O I
10.1039/b210963h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation of 2',3'-epimino-carbocyclic analogues of adenosine is reported. The reaction of p-tosyl azide with N-substituted 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH) (1a) provided aziridine-fused ABH (2), which was converted to 2',3'-epimino-carbocyclic nucleosides (11).
引用
收藏
页码:452 / 453
页数:2
相关论文
共 25 条
[1]  
AGROFOGLIO LA, 2000, CHEM REV, V100, P4319
[2]   1',6'-METHANO CARBOCYCLIC THYMIDINE - SYNTHESIS, X-RAY CRYSTAL-STRUCTURE, AND EFFECT ON NUCLEIC-ACID DUPLEX STABILITY [J].
ALTMANN, KH ;
IMWINKELRIED, R ;
KESSELRING, R ;
RIHS, G .
TETRAHEDRON LETTERS, 1994, 35 (41) :7625-7628
[3]   4',6'-METHANO CARBOCYCLIC THYMIDINE - A CONFORMATIONALLY CONSTRAINED BUILDING-BLOCK FOR OLIGONUCLEOTIDES [J].
ALTMANN, KH ;
KESSELRING, R ;
FRANCOTTE, E ;
RIHS, G .
TETRAHEDRON LETTERS, 1994, 35 (15) :2331-2334
[4]   Nucleosides with furanyl scaffolds [J].
Bera, S ;
Nair, V .
TETRAHEDRON, 2002, 58 (24) :4865-4871
[5]   Synthesis of a conformationally locked version of puromycin amino nucleoside [J].
Choi, Y ;
George, C ;
Strazewski, P ;
Marquez, VE .
ORGANIC LETTERS, 2002, 4 (04) :589-592
[6]  
FERRERO M, 2001, CURR MED CHEM, V84, P385
[7]   A concise access to 6-azabicyclo[3.1.0] hexanes via high-pressure promoted cycloaddition reaction of azides to ABH [J].
Ishikura, M ;
Kudo, S ;
Hino, A ;
Ohnuki, N ;
Katagiri, N .
HETEROCYCLES, 2000, 53 (07) :1499-1504
[8]  
ISHIKURA M, 2002, IN PRESS HETEROCYCLE, V58
[9]   Methanocarba analogues of purine nucleosides as potent and selective adenosine receptor agonists [J].
Jacobson, KA ;
Ji, XD ;
Li, AH ;
Melman, N ;
Siddiqui, MA ;
Shin, KJ ;
Marquez, VE ;
Ravi, RG .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (11) :2196-2203
[10]   The first synthesis of a 2′,3′-methane carbocyclic nucleoside [J].
Katagiri, N ;
Yamatoya, Y ;
Ishikura, M .
TETRAHEDRON LETTERS, 1999, 40 (51) :9069-9072