Organotransition metal modified sugars -: Part 12 -: Hydroxynaphthyl C-glycosides via chromium-mediated benzannulation of a sugar alkyne

被引：28

作者：

Paetsch, D ^{[1
]}

Dötz, KH ^{[1
]}

机构：

[1] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 03期

关键词：

benzannulation; carbenes and carbenoids; carbohydrates; chromium carbenes; glycosides;

D O I：

10.1016/S0040-4039(98)02488-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzannulation of C-ethynyl glucoside 1 with electrophilic chromium carbene 2 affords Cr(CO)(3)-coordinated hydroxynaphthyl C-glycoside 3. The metal carbonyl fragment can be shifted by haptotropic migration or removed upon oxidation to give aryl C-glycosides 4 and 5. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：487 / 488

页数：2

共 11 条

[1] SYNTHESIS OF NAPHTHOL SKELETON FROM PENTACARBONYL[METHOXY(PHENYL)CARBENE]CHROMIUM(0) AND TOLAN [J].

DOTZ, KH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (09) :644-645

[2] CARBENE COMPLEXES IN ORGANIC-SYNTHESIS [J].

DOTZ, KH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (08) :587-608

[3]

DOTZ KH, UNPUB

[4] TRANSITION-METAL CARBENE COMPLEXES .93. PENTACARBONYL(DIARYLCARBENE) COMPLEXES OF CHROMIUM(0) AND TUNGSTEN(0) [J].

FISCHER, EO ;

HELD, W ;

KREISSL, FR ;

FRANK, A ;

HUTTNER, G .

CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (02) :656-666

[5]

Hacksell U, 1985, Prog Med Chem, V22, P1, DOI 10.1016/S0079-6468(08)70228-5

[6]

JARAMILLO J, 1994, SYNTHESIS-STUTTGART, P1

[7]

KRAUS GA, 1988, J ORG CHEM, V53, P742

[8] RECENT DEVELOPMENTS IN THE SYNTHESIS OF C-GLYCOSIDES [J].

POSTEMA, MHD .

TETRAHEDRON, 1992, 48 (40) :8545-8599

[9] C-arylglycosides via a benzannulation mediated by Fischer chromium carbene complexes [J].

Pulley, SR ;

Carey, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) :5275-5279

[10]

Suzuki K., 1993, RECENT PROGR CHEM SY, V2, P352

← 1 2 →