A new access to C-arylglycosides related to the gilvocarcins

被引：18

作者：

Cordero-Vargas, A ^{[1
]}

Quiclet-Sire, B ^{[1
]}

Zard, SZ ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, Synth Organ Lab, F-91128 Palaiseau, France

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 39期

关键词：

C-arylglycosides; gilvocarcins; xanthate; addition; cyclization; aromatisation;

D O I：

10.1016/j.tetlet.2004.08.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

A new strategy has been developed for the synthesis of C-aryl glycosides based on a xanthate-mediated free radical addition-cyclization sequence of an acetophenone xanthate to a vinylic carbohydrate followed by aromatization. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：7335 / 7338

页数：4

共 22 条

[1]

Formal radical cyclization onto benzene rings:: a general method and its use in the synthesis of ent-nocardione A [J].

Clive, DLJ ;

Fletcher, SP ;

Liu, DZ .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3282-3293

[2]

Cordero-Vargas A., 2003, ORG LETT, V5, P3717, DOI DOI 10.1021/OL035394O

[3]

STEREOSELECTIVE SYNTHESIS OF ALPHA-C-ALLYL-GLYCOPYRANODISES [J].

GIANNIS, A ;

SANDHOFF, K .

TETRAHEDRON LETTERS, 1985, 26 (12) :1479-1482

[4]

CYCLIZATION OF HYDROXY ENOL ETHERS - A STEREOCONTROLLED APPROACH TO 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID CONTAINING DISACCHARIDES [J].

HAUDRECHY, A ;

SINAY, P .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4142-4151

[5]

TOTAL SYNTHESIS OF THE GILVOCARCINS [J].

HOSOYA, T ;

TAKASHIRO, E ;

MATSUMOTO, T ;

SUZUKI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :1004-1015

[6]

ASYMMETRIC-SYNTHESIS OF THE KEY INTERMEDIATES LEADING TO (-)-APHANORPHINE AND (-)-EPTAZOCINE [J].

HULME, AN ;

HENRY, SS ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1265-1270

[7]

JARAMILLO C, 1994, SYNTHESIS-STUTTGART, P1

[8]

INTRODUCTION OF UNSATURATED LINKAGES INTO SOME CARBOHYDRATES BY PYROLYSIS OF CYCLIC ORTHOFORMIC ESTERS [J].

JOSAN, JS ;

EASTWOOD, FW .

CARBOHYDRATE RESEARCH, 1968, 7 (02) :161-&

[9]

Kaoudi T, 2000, ANGEW CHEM INT EDIT, V39, P731, DOI 10.1002/(SICI)1521-3773(20000218)39:4<731::AID-ANIE731>3.3.CO

[10]

2-L

← 1 2 3 →