Enantioselective synthesis of homocarbocyclic-2′-oxo-3′-azanucleosides

被引：31

作者：

Chiacchio, U

Saita, MG

Crispino, L

Gumina, G

Mangiafico, S

Pistarà, V

Romeo, G

Piperno, A

De Clercq, E

机构：

[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy

[2] Med Univ S Carolina, Dept Pharmaceut Sci, Charleston, SC 29425 USA

[3] Univ Messina, Dipartimento Farm Chim, I-98168 Messina, Italy

[4] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium

来源：

TETRAHEDRON | 2006年 / 62卷 / 06期

关键词：

nucleosides; 1,3-dipolar cycloaddition; N-glycosyl nitrones;

D O I：

10.1016/j.tet.2005.10.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of homocarbocyclic-2'oxo-3'-azanucleosides has been performed by cycloaddition reaction of the N-glycosyl nitrones with allyl nucleobases. The use of nitrones originated from two different carbohydrates, the N-ribosyl nitrone and the N-mannosyl nitrone, proceeded in a stereocontrolled and predictable manner with a good degree of enantioselectivity, so allowing an easy entry to both enantiomers. (c) 2005 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1171 / 1181

页数：11

相关论文

共 22 条

[11] BACKBONE MODIFICATIONS IN OLIGONUCLEOTIDES AND PEPTIDE NUCLEIC-ACID SYSTEMS [J].

DEMESMAEKER, A ;

ALTMANN, KH ;

WALDNER, A ;

WENDEBORN, S .

CURRENT OPINION IN STRUCTURAL BIOLOGY, 1995, 5 (03) :343-355

[12] Unusually strong binding of a designed transition-state analog to a base-excision DNA repair protein [J].

Deng, L ;

Scharer, OD ;

Verdine, GL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) :7865-7866

[13] CHEMISTRY OF POTENTIALLY PREBIOLOGICAL NATURAL-PRODUCTS [J].

ESCHENMOSER, A ;

LOEWENTHAL, E .

CHEMICAL SOCIETY REVIEWS, 1992, 21 (01) :1-16

[14] Homo-N-nucleosides: Incorporation into oligonucleotides and antiviral activity. [J].

Hossain, N ;

Hendrix, C ;

Lescrinier, E ;

VanAerschot, A ;

Busson, R ;

DeClercq, E ;

Herdewijn, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (13) :1465-1468

[15] Homo-N-oligonucleotides (N1/N9-C1′ methylene bridge oligonucleotides):: Nucleic acids with left-handed helicity [J].

Ishiyama, K ;

Smyth, GE ;

Ueda, T ;

Masutomi, Y ;

Ohgi, T ;

Yano, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7476-7485

[16] ASYMMETRIC TOTAL SYNTHESIS OF (+)-NEGAMYCIN AND (-)-3-EPINEGAMYCIN VIA ENANTIOSELECTIVE 1,3-DIPOLAR CYCLO-ADDITION [J].

KASAHARA, K ;

IIDA, H ;

KIBAYASHI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (09) :2225-2233

[17] Structural modifications toward improved antisense oligonucleotides [J].

Matteucci, M .

PERSPECTIVES IN DRUG DISCOVERY AND DESIGN, 1996, 4 :1-16

[18]

Merino Pedro, 2002, Current Medicinal Chemistry - Anti-Infective Agents, V1, P389, DOI 10.2174/1568012023354677

[19] Synthesis of 1′-homo-N-nucleosides from hexitols [J].

Saladino, R ;

Ciambecchini, U ;

Hanessian, S .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) :4401-4405

[20] Chemical etiology of nucleic acid structure:: The α-threofuranosyl-(3′→2′) oligonucleotide system [J].

Schöning, KU ;

Scholz, P ;

Guntha, S ;

Wu, X ;

Krishnamurthy, R ;

Eschenmoser, A .

SCIENCE, 2000, 290 (5495) :1347-1351