Tandem nucleophilic addition/cyclization reaction in the synthesis of ketimine-type iminosugars

被引:12
作者
Behr, Jean-Bernard [1 ]
Kalla, Adel [1 ]
Harakat, Dominique [1 ]
Plantier-Royon, Richard [1 ]
机构
[1] CNRS, UFR Sci, ICMR, F-51687 Reims 2, France
关键词
D O I
10.1021/jo702616x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The biological activity of unsaturated iminosugars has not yet been extensively studied because of a lack of general synthetic methods. A practical synthesis of these cyclic ketimine sugars was developed, which was based on a tandem addition-cyclization reaction of a Grignard reagent to a omega-methanesulfonylglycononitrile.
引用
收藏
页码:3612 / 3615
页数:4
相关论文
共 49 条
[1]   Emerging roles of carbohydrates and glycomimetics in anticancer drug design [J].
Barchi, JJ .
CURRENT PHARMACEUTICAL DESIGN, 2000, 6 (04) :485-501
[2]   Inhibition of chitin synthase by a series of 7-deoxycasuarine stereoisomers designed as constrained analogues of the potent inhibitor 6-deoxyhomoDMDP [J].
Behr, J. -B. ;
Gainvors-Claisse, A. ;
Belarbi, A. .
NATURAL PRODUCT RESEARCH, 2006, 20 (14) :1308-1314
[3]  
Behr J.-B., 2003, Current Medicinal Chemistry - Anti-Infective Agents, V2, P173, DOI 10.2174/1568012033483114
[4]   Synthesis of 2',3'-dihydrosolanesyl analogues of β-D-arabinofuranosyl-1-monophosphoryldecaprenoI with promising antimycobacterial activity [J].
Bosco, Michael ;
Bisseret, Philippe ;
Constant, Patricia ;
Eustache, Jacques .
TETRAHEDRON LETTERS, 2007, 48 (01) :153-157
[5]   Stereoselective synthesis of arabinose-derived phosphonates [J].
Bouix, C ;
Bisseret, P ;
Eustache, J .
TETRAHEDRON LETTERS, 1998, 39 (08) :825-828
[6]   POTENTIAL GLYCOSIDASE INHIBITORS - SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO DERIVATIVES OF D-GLUCITOL, D-XYLITOL AND L-XYLITOL, D-ALLITOL AND L-ALLITOL, D-TALITOL AND L-TALITOL, AND D-GULITOL [J].
BUCHANAN, JG ;
LUMBARD, KW ;
STURGEON, RJ ;
THOMPSON, DK ;
WIGHTMAN, RH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :699-706
[7]   EFFECT OF BENZENE IN GRIGNARD REACTIONS OF NITRILE [J].
CANONNE, P ;
FOSCOLOS, GB ;
LEMAY, G .
TETRAHEDRON LETTERS, 1980, 21 (02) :155-158
[8]   Highly diastereoselective additions to polyhydroxylated pyrrolidine cyclic imines: Ready elaboration of aza-sugar scaffolds to create diverse carbohydrate-processing enzyme probes [J].
Chapman, TM ;
Courtney, S ;
Hay, P ;
Davis, BG .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (14) :3397-3414
[9]   REACTIVITY OF ORGANOMETALLIC COMPLEXES - CONTROL OF ADDITION-DEPROTONATION COMPETITION IN REACTION OF NITRILES WITH N-PRMGBR-LICLO4 COMPLEX [J].
CHASTRETTE, M ;
AMOUROUX, R ;
SUBIT, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 99 (03) :C41-C43
[10]   Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: Effects of the bulky protecting groups to enforce facial selectivity [J].
Choi, WJ ;
Moon, HR ;
Kim, HO ;
Yoo, BN ;
Lee, JA ;
Shin, DH ;
Jeong, LS .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2634-2636