Synthesis and conformational and biological aspects of carbasugars

被引:307
作者
Arjona, Odon
Gomez, Ana M.
Cristobal Lopez, J.
Plumet, Joaquin
机构
[1] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
[2] Univ Complutense, Dept Quim Organ, Fac Quim, E-28040 Madrid, Spain
关键词
D O I
10.1021/cr0203701
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review covers the progress made in the chemistry, synthesis and biology of carbasugars until May 2004. It includes the extensively studied carbapyranoses as well as the scarcely considered carbafuranoses. Specific topics discussed include the natural occurrence of carbasugars, biosynthesis and biological activity of carbasugars, conformational analysis of carbasugars, and the compilation of synthetic methods of carbafuranoses and carbapyranoses.
引用
收藏
页码:1919 / 2036
页数:118
相关论文
共 730 条
[1]   A stereodivergent synthesis of (+/-)-cyclophellitol and (1R*,6S*)-cyclophellitol from the 7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid. [J].
Acena, JL ;
deAlba, E ;
Arjona, O ;
Plumet, J .
TETRAHEDRON LETTERS, 1996, 37 (17) :3043-3044
[2]   STRAIN-DIRECTED BRIDGE CLEAVAGE OF (PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - APPLICATION TO THE TOTAL SYNTHESIS OF CARBA-ALPHA-DL-GLUCOPYRANOSE [J].
ACENA, JL ;
ARJONA, O ;
DELAPRADILLA, RF ;
PLUMET, J ;
VISO, A .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1945-1946
[3]   Unexpected one-pot epoxy sulfone-enaminone transformation.: Synthesis of 5a-carba-β-mannopyranosylamine [J].
Aceña, JL ;
Arjona, O ;
Mañas, R ;
Plumet, J .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) :2580-2582
[4]   A STEREODIVERGENT ACCESS TO NATURALLY-OCCURRING AMINOCARBASUGARS FROM (PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - TOTAL SYNTHESIS OF PENTA-N,O-ACETYL-(+/-)-VALIDAMINE AND ITS C-1 AND C-2 STEREOISOMERS [J].
ACENA, JL ;
ARJONA, O ;
DELAPRADILLA, RF ;
PLUMET, J ;
VISO, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6419-6424
[5]   Total syntheses of (+/-)-cyclophellitol and (1R*,6S*)-cyclophellitol [J].
Acena, JL ;
Arjona, O ;
Plumet, J .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3360-3364
[6]   Analysis of the polysaccharide components of the lipopolysaccharide fraction of Pseudomonas caryophylli [J].
Adinolfi, M ;
Corsaro, MM ;
DeCastro, C ;
Evidente, A ;
Lanzetta, R ;
Lavermicocca, P ;
Parrilli, M .
CARBOHYDRATE RESEARCH, 1996, 284 (01) :119-133
[7]   Caryose: A carbocyclic monosaccharide from Pseudomonas caryophylli [J].
Adinolfi, M ;
Corsaro, MM ;
DeCastro, C ;
Evidente, A ;
Lanzetta, R ;
Molinaro, A ;
Parrilli, M .
CARBOHYDRATE RESEARCH, 1996, 284 (01) :111-118
[8]   A novel synthesis of (±) 2-epi-validamine [J].
Afarinkia, K ;
Mahmood, F .
TETRAHEDRON LETTERS, 1998, 39 (40) :7413-7414
[9]   (1R,3R)-2-methylene-1,3-dithiolane 1,3-dioxide:: a highly reactive and highly selective chiral ketene equivalent in cycloaddition reactions with a broad range of dienes [J].
Aggarwal, VK ;
Gultekin, Z ;
Grainger, RS ;
Adams, H ;
Spargo, PL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (17) :2771-2781
[10]   Olefin metathesis route to antiviral nucleosides [J].
Agrofoglio, LA ;
Nolan, SP .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2005, 5 (15) :1541-1558