First total synthesis of (+)-3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) from a non-carbohydrate source

被引:22
作者
Banwell, M [1 ]
De Savi, C
Watson, K
机构
[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
[2] Monash Univ, Dept Chem, Biota Chem Lab, Clayton, Vic 3168, Australia
关键词
D O I
10.1039/a801889h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantiopure cis-1,2-dihydrocatechol 2, a product obtained by microbial oxidation of chlorobenzene, has been converted into KDN 1 via a ten step reaction sequence.
引用
收藏
页码:1189 / 1190
页数:2
相关论文
共 31 条
[1]   Diastereoselective routes to side-chain truncated analogues of N-acetylneuraminic acid [J].
Banwell, M ;
De Savi, C ;
Hockless, D ;
Watson, K .
CHEMICAL COMMUNICATIONS, 1998, (06) :645-646
[2]   DEOXY-NITROSUGARS .15. SYNTHESIS OF N-ACETYLNEURAMINIC ACID AND N-ACETYL-4-EPINEURAMINIC ACID [J].
BAUMBERGER, F ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1986, 69 (05) :1205-1215
[3]  
Brown S.M., 1993, ORGANIC SYNTHESIS TH, V2, P113
[4]   THE USE OF CYCLOHEXA-3,5-DIENE-1,2-DIOLS IN ENANTIOSPECIFIC SYNTHESIS [J].
CARLESS, HAJ .
TETRAHEDRON-ASYMMETRY, 1992, 3 (07) :795-826
[5]   INDIUM-MEDIATED COUPLING OF ALPHA-(BROMOMETHYL)ACRYLIC ACID WITH CARBONYL-COMPOUNDS IN AQUEOUS-MEDIA - CONCISE SYNTHESES OF (+)-3-DEOXY-D-GLYCERO-D-GALACTO-NONULOSONIC ACID AND N-ACETYLNEURAMINIC ACID [J].
CHAN, TH ;
LEE, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4228-4232
[6]   Synthesis of phosphonic acid analogues of sialic acids (Neu5Ac and KDN) as potential sialidase inhibitors [J].
Chan, TH ;
Xin, YC ;
vonItzstein, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) :3500-3504
[7]   INSTALLATION OF THE PYRUVATE UNIT IN GLYCIDIC ALDEHYDES VIA A WITTIG OLEFINATION MICHAEL ADDITION SEQUENCE UTILIZING A THIAZOLE-ARMED CARBONYL YLID - A NEW STEREOSELECTIVE ROUTE TO 3-DEOXY-2-ULOSONIC ACIDS AND THE TOTAL SYNTHESIS OF DAH, KDN, AND 4-EPI-KDN [J].
DONDONI, A ;
MARRA, A ;
MERINO, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3324-3336
[8]   Synthetic studies on sialoglycoconjugates .89. Synthesis of ganglioside GM(3) and KDN-GM(3) containing different carbon-chain length fatty acyl groups at the ceramide residue [J].
Hasegawa, A ;
Suzuki, N ;
Kozawa, F ;
Ishida, H ;
Kiso, M .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1996, 15 (05) :639-648
[9]   Current status and future perspectives of cyclohexadiene-cis-diols in organic synthesis: Versatile intermediates in the concise design of natural products [J].
Hudlicky, T ;
Thorpe, AJ .
CHEMICAL COMMUNICATIONS, 1996, (17) :1993-2000
[10]  
HUDLICKY T, 1991, ISR J CHEM, V31, P229