An in-depth study on ring-closing metathesis of carbohydrate-derived α-alkoxyacrylates:: Efficient syntheses of DAH, KDO, and 2-deoxy-β-KDO

被引：30

作者：

Hekking, Koen F. W. ^{[1
]}

Moelands, Marcel A. H. ^{[1
]}

van Delft, Floris L. ^{[1
]}

Rutjes, Floris P. J. T. ^{[1
]}

机构：

[1] Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 17期

关键词：

D O I：

10.1021/jo060913x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel, efficient synthetic pathways to DAH, KDO, and 2-deoxy-beta-KDO are described. Ring-closing metathesis (RCM) of highly functionalized alpha-alkoxyacrylate fragments resulted in a series of synthetically versatile oxygen heterocyclic intermediates. Further functionalization of the resulting enol ether double bond and subsequent deprotection provided the natural products in high overall yields, starting from commercially available protected sugars.

引用

页码：6444 / 6450

页数：7

共 55 条

[1] Non-metathetic behavior patterns of Grubbs' carbene [J].

Alcaide, B ;

Almendros, P .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (06) :1259-1262

[2] 4-[(4-methylphenyl)sulfonyl]-l-(triphenylphosphoranylidene)-2-butanone as a convenient precursor for a new formal synthesis of KDO [J].

Barco, A ;

Bassetti, L ;

Benetti, S ;

Bertolasi, V ;

De Risi, C ;

Marchetti, P ;

Pollini, GP .

TETRAHEDRON, 2002, 58 (42) :8553-8558

[3] 2,3,5-TRI-O-BENZYL-D-RIBOSYL AND -L-ARABINOSYL BROMIDES [J].

BARKER, R ;

FLETCHER, HG .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (11) :4605-&

[4] The invention of radical reactions .38. Homologation of carboxylic acids with acrylamide and synthetic studies of 3-Deoxy-D-arabino-2-heptulosonic acid (DAH) and its 4-epimer [J].

Barton, DHR ;

Liu, WS .

TETRAHEDRON, 1997, 53 (36) :12067-12088

[5] THE SHIKIMATE PATHWAY - A METABOLIC TREE WITH MANY BRANCHES [J].

BENTLEY, R .

CRITICAL REVIEWS IN BIOCHEMISTRY AND MOLECULAR BIOLOGY, 1990, 25 (05) :307-384

[6] The Cl2(PCy3)(IMes)Ru(=CHPh) catalyst:: olefin metathesis versus olefin isomerization [J].

Bourgeois, D ;

Pancrazi, A ;

Nolan, SP ;

Prunet, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 643 :247-252

[7] 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

[8] A 2-DEOXY ANALOG OF KDO AS THE 1ST INHIBITOR OF THE ENZYME CMP-KDO SYNTHETASE [J].

CLAESSON, A ;

LUTHMAN, K ;

GUSTAFSSON, K ;

BONDESSON, G .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1987, 143 (03) :1063-1068

[9] Experiences with the Shikimate-pathway enzymes as targets for rational drug design [J].

Coggins, JR ;

Abell, C ;

Evan, LB ;

Frederickson, M ;

Robinson, DA ;

Roszak, AW ;

Lapthorn, AP .

BIOCHEMICAL SOCIETY TRANSACTIONS, 2003, 31 :548-552

[10] Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues [J].

Crestia, D ;

Demuynck, C ;

Bolte, J .

TETRAHEDRON, 2004, 60 (10) :2417-2425

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