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

被引:56
作者
Ezzitouni, A [1 ]
Russ, P [1 ]
Marquez, VE [1 ]
机构
[1] NCI,MED CHEM LAB,DIV BASIC SCI,NIH,BETHESDA,MD 20892
关键词
D O I
10.1021/jo962124t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
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页码:4870 / 4873
页数:4
相关论文
共 15 条
[1]   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
[2]   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-+
[3]   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
[4]   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
[5]  
DENIS JN, 1979, TETRAHEDRON LETT, P2697
[6]  
EZZITOUNI A, IN PRESS J CHEM S P1
[7]   THEORETICAL AND EXPERIMENTAL STUDIES OF REGIOSELECTIVITY IN SELENOXIDE ELIMINATION [J].
KONDO, N ;
FUENO, H ;
FUJIMOTO, H ;
MAKINO, M ;
NAKAOKA, H ;
AOKI, I ;
UEMURA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5254-5263
[8]   TOTAL SYNTHESIS OF (-)-NEPLANOCIN-A [J].
MARQUEZ, VE ;
LIM, MI ;
TSENG, CKH ;
MARKOVAC, A ;
PRIEST, MA ;
KHAN, MS ;
KASKAR, B .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5709-5714
[9]   Nucleosides with a twist. Can fixed forms of sugar ring pucker influence biological activity in nucleosides and oligonucleotides? [J].
Marquez, VE ;
Siddiqui, MA ;
Ezzitouni, A ;
Russ, P ;
Wang, JY ;
Wagner, RW ;
Matteucci, MD .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (19) :3739-3747
[10]   Hydroxyl- versus amide-directed cyclopropanation from the allylic position in 1-nydroxy-4-N-acyl-cyclopentenes under modified Simmons-Smith conditions [J].
Russ, P ;
Ezzitouni, A ;
Marquez, VE .
TETRAHEDRON LETTERS, 1997, 38 (05) :723-726