A SIMPLE APPROACH TO 1',1'A-METHANO CARBOCYCLIC THYMIDINE

被引：34

作者：

EZZITOUNI, A ^{[1
]}

BARCHI, JJ ^{[1
]}

MARQUEZ, VE ^{[1
]}

机构：

[1] NCI,DIV CANC TREATMENT,MED CHEM LAB,DEV THERAPEUT PROGRAM,BETHESDA,MD 20892

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 13期

关键词：

D O I：

10.1039/c39950001345

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective synthesis of 1',1'a-methano carbocyclic thymidine, a rigid mdleculethat mimics thymidine's 2/-endo/3'-exo (South) conformation, is efficiently synthesized from chiral 2-benzyloxymethylcyclopent-3-enol.

引用

页码：1345 / 1346

页数：2

共 17 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] NUCLEOSIDES AND NUCLEOTIDES .122. 2'-C-CYANO-2'-DEOXY-1-BETA-D-ARABINOFURANOSYLCYTOSINE AND ITS DERIVATIVES - A NEW CLASS OF NUCLEOSIDE WITH A BROAD ANTITUMOR SPECTRUM [J].

AZUMA, A ;

NAKAJIMA, Y ;

NISHIZONO, N ;

MINAKAWA, N ;

SUZUKI, M ;

HANAOKA, K ;

KOBAYASHI, T ;

TANAKA, M ;

SASAKI, T ;

MATSUDA, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (26) :4183-4189

[4] SYNTHESIS AND BIOLOGICAL PROPERTIES OF (+)- AND (-)-(E)-5-(2-BROMOVINYL)-2'-DEOXY-1'-ALPHA-CARBAURIDINE [J].

BALZARINI, J ;

BAUMGARTNER, H ;

BODENTEICH, M ;

DECLERCQ, E ;

GRIENGL, H .

NUCLEOSIDES & NUCLEOTIDES, 1989, 8 (5-6) :855-858

[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]

GAIS HJ, 1986, LIEBIGS ANN CHEM, P687

[8] CRYSTAL AND MOLECULAR-STRUCTURE OF (+)-CARBA-THYMIDINE, C11H16N2O6 [J].

KALMAN, A ;

KORITSANSZKY, T ;

BERES, J ;

SAGI, G .

NUCLEOSIDES & NUCLEOTIDES, 1990, 9 (02) :235-243

[9] CARBOCYCLIC NUCLEOSIDES [J].

MARQUEZ, VE ;

LIM, MI .

MEDICINAL RESEARCH REVIEWS, 1986, 6 (01) :1-40

[10]

NACE HR, 1962, ORG REACTIONS, V12, P57

← 1 2 →