A remarkably simple chemicoenzymatic approach to structurally complex bicyclo[3.1.0]hexane carbocyclic nucleosides

被引：34

作者：

Moon, HR ^{[1
]}

Ford, H ^{[1
]}

Marquez, VE ^{[1
]}

机构：

[1] NCI, Frederick Canc Res & Dev Ctr, Med Chem Lab, Div Basic Sci, Frederick, MD 21702 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 24期

关键词：

D O I：

10.1021/ol000238s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Intramolecular cyclopropanation of a carbene engendered from the corresponding diazo beta -ketoester produced the desired bicyclo[3.1.0]hexane pseudosugar. Purine nucleosides obtained via Mitsunobu coupling were resolved with adenosine deaminase. The requisite beta -ketoester was assembled in one step from ethyl acetoacetate and acrolein.

引用

页码：3793 / 3796

页数：4

共 26 条

[1] 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

[2] 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

[3] CONFORMATIONAL-ANALYSIS OF SUGAR RING IN NUCLEOSIDES AND NUCLEOTIDES - NEW DESCRIPTION USING CONCEPT OF PSEUDOROTATION [J].

ALTONA, C ;

SUNDARALINGAM, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (23) :8205-+

[4] Crystal structures of B-DNA with incorporated 2′-deoxy-2′-fluoro-arabino-furanosyl thymines:: implications of conformational preorganization for duplex stability [J].

Berger, I ;

Tereshko, V ;

Ikeda, H ;

Marquez, VE ;

Egli, M .

NUCLEIC ACIDS RESEARCH, 1998, 26 (10) :2473-2480

[5] USE OF DIETHYLAMINOSULPHUR TRIFLUORIDE (DAST) IN THE PREPARATION OF SYNTHONS OF CARBOCYCLIC NUCLEOSIDES [J].

BIGGADIKE, K ;

BORTHWICK, AD ;

EVANS, D ;

EXALL, AM ;

KIRK, BE ;

ROBERTS, SM ;

STEPHENSON, L ;

YOUDS, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03) :549-554

[6] SYNTHESIS OF FLUORINATED CARBOCYCLIC NUCLEOSIDES - PREPARATION OF CARBOCYCLIC 1-(2'-DEOXY-6'-FLUORORIBOFURANOSYL)-5-IODOURACILS [J].

BIGGADIKE, K ;

BORTHWICK, AD ;

EXALL, AM ;

KIRK, BE ;

ROBERTS, SM ;

YOUDS, P ;

SLAWIN, AMZ ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (04) :255-256

[7] A SIMPLE APPROACH TO 1',1'A-METHANO CARBOCYCLIC THYMIDINE [J].

EZZITOUNI, A ;

BARCHI, JJ ;

MARQUEZ, VE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (13) :1345-1346

[8] Conformationally locked carbocyclic nucleosides built on a bicyclo[3.1.0]hexane template with a fixed Southern conformation. Synthesis and antiviral activity [J].

Ezzitouni, A ;

Marquez, VE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (07) :1073-1078

[9] (1S,2R)-[(benzyloxy)methyl]cyclopent-3-enol. A versatile synthon for the preparation of 4',1'a-methano- and 1',1'a-methanocarbocyclic nucleosides [J].

Ezzitouni, A ;

Russ, P ;

Marquez, VE .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4870-4873

[10] SYNTHESIS OF ENANTIOMERICALLY PURE BICYCLO[3.1.0]HEXANES FROM D-RIBOSE BY INTRAMOLECULAR CYCLOPROPANATION [J].

GALLOS, JK ;

KOFTIS, TV ;

KOUMBIS, AE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06) :611-612

← 1 2 3 →