Regioselective and enantiospecific rhodium-catalyzed allylic amination with thymine: synthesis of a new conformationally rigid nucleoside

被引:25
作者
Evans, PA [1 ]
Lai, KW [1 ]
Zhang, HR [1 ]
Huffman, JC [1 ]
机构
[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
关键词
D O I
10.1039/b513083b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The regioselective and enantiospecific rhodium-catalyzed allylic amination of secondary allylic carbonates with N-3-benzoyl thymine in conjunction with a stereoselective free radical cyclization provides a convenient method for the construction of a new conformationally rigid nucleoside.
引用
收藏
页码:844 / 846
页数:3
相关论文
共 27 条
[1]   Palladium-assisted routes to nucleosides [J].
Agrofoglio, LA ;
Gillaizeau, I ;
Saito, Y .
CHEMICAL REVIEWS, 2003, 103 (05) :1875-1916
[2]   New antiviral nucleoside prodrugs await application [J].
Anastasi, C ;
Quéléver, G ;
Burlet, S ;
Garino, C ;
Souard, F ;
Kraus, JL .
CURRENT MEDICINAL CHEMISTRY, 2003, 10 (18) :1825-1843
[3]   Synthesis and antiviral evaluation of cis-substituted cyclohexenyl and cyclohexanyl-nucleosides [J].
Barral, K ;
Courcambeck, J ;
Pèpe, G ;
Balzarini, J ;
Neyts, J ;
De Clercq, E ;
Camplo, M .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (02) :450-456
[4]   HIGHLY DIASTEREOSELECTIVE FORMATION OF SUBSTITUTED INDOLIZIDINES AND QUINOLIZIDINES BY RADICAL CYCLIZATION [J].
BECKWITH, ALJ ;
JOSEPH, SP ;
MAYADUNNE, RTA .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4198-4199
[5]   A conformationally locked analogue of the anti-HIV agent stavudine. An important correlation between pseudorotation and maximum amplitude [J].
Choi, YS ;
George, C ;
Comin, MJ ;
Barchi, JJ ;
Kim, HS ;
Jacobson, KA ;
Balzarini, J ;
Mitsuya, H ;
Boyer, PL ;
Hughes, SH ;
Marquez, VE .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (15) :3292-3299
[6]   SHORT ENANTIOSELECTIVE SYNTHESIS OF (-)-OVALICIN, A POTENT INHIBITOR OF ANGIOGENESIS, USING SUBSTRATE-ENHANCED CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
COREY, EJ ;
GUZMANPEREZ, A ;
NOE, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12109-12110
[7]   Nucleoside anticancer drugs: the role of nucleoside transporters in resistance to cancer chemotherapy [J].
Damaraju, VL ;
Damaraju, S ;
Young, JD ;
Baldwin, SA ;
Mackey, J ;
Sawyer, MB ;
Cass, CE .
ONCOGENE, 2003, 22 (47) :7524-7536
[8]   Recent advances in the Mitsunobu reaction: Modified reagents and the quest for chromatography-free separation [J].
Dembinski, R .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (13) :2763-2772
[9]   Stereoselective construction of trans-disubstituted azabicycles using oxauracil as a novel free radical acceptor [J].
Evans, PA ;
Manangan, T ;
Rheingold, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) :11009-11010
[10]   Stereoselective construction of trans-disubstituted azabicycles using oxauracil as a novel free radical acceptor (vol 122, pg 11009, 2000) [J].
Evans, PA ;
Manangan, T ;
Rheingold, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16745-16745