Formal synthesis of (+)3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via desymmetrization by ring-closing metathesis

被引：56
作者：
Burke, SD [1 ]
Voight, EA [1 ]
机构：
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
来源：
ORGANIC LETTERS | 2001年 / 3卷 / 02期
关键词：
D O I：
10.1021/ol006887l
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Formal synthesis of the naturally occurring deaminated sialic acid KDN, a potential oncofetal antigen, has been accomplished in 45% overall yield via a novel ketalization/ring-closing metathesis sequence, The rapid introduction of all oxygen functionality in a completely stereocontrolled manner exploited a rigid 6,8-dioxabicyclo[3.2.1]oct-2-ene ring system. This general synthetic strategy should provide access to a number of KDN and sialic acid analogues.
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页码：237 / 240
页数：4
相关论文
共 57 条
[1]  
Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[2]   Enantioselective synthesis of (S)-2-(aminomethyl)butanedioic acid using chiral beta-alanine alpha-enolate equivalents [J].
Arvanitis, E ;
Motevalli, M ;
Wyatt, PB .
TETRAHEDRON LETTERS, 1996, 37 (24) :4277-4280
[3]   SIALYL ALDOLASE IN ORGANIC-SYNTHESIS - FROM THE TROUT EGG ACID, 3-DEOXY-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID (KDN), TO BRANCHED-CHAIN HIGHER KETOSES AS POSSIBLE NEW CHIRONS [J].
AUGE, C ;
GAUTHERON, C ;
DAVID, S ;
MALLERON, A ;
CAVAYE, B ;
BOUXOM, B .
TETRAHEDRON, 1990, 46 (01) :201-214
[4]   SCOPE AND LIMITATIONS OF THE ALDOL CONDENSATION CATALYZED BY IMMOBILIZED ACYLNEURAMINATE PYRUVATE LYASE [J].
AUGE, C ;
BOUXOM, B ;
CAVAYE, B ;
GAUTHERON, C .
TETRAHEDRON LETTERS, 1989, 30 (17) :2217-2220
[5]   Enantioselective synthesis of 2-substituted 4-aminobutanoic acid (GABA) analogues via cyanomethylation of chiral enolates [J].
Azam, S ;
DSouza, AA ;
Wyatt, PB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (07) :621-627
[6]   First total synthesis of (+)-3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) from a non-carbohydrate source [J].
Banwell, M ;
De Savi, C ;
Watson, K .
CHEMICAL COMMUNICATIONS, 1998, (11) :1189-1190
[7]   A new ligand class for the asymmetric dihydroxylation of olefins [J].
Becker, H ;
Sharpless, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :448-451
[8]  
Burke S.D., 1999, ORG LETT, V1, P1827
[9]   Total synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and 2-deoxy-β-KDO [J].
Burke, SD ;
Sametz, GM .
ORGANIC LETTERS, 1999, 1 (01) :71-74
[10]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
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