Addition of allylstannanes to glycal epoxides.: A diastereoselective approach to β-C-glycosidation

被引：50

作者：

Evans, DA ^{[1
]}

Trotter, BW ^{[1
]}

Côté, B ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 13期

基金：

加拿大自然科学与工程研究理事会; 美国国家科学基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(98)00138-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the synthesis of beta-C-allyl glycosides has been developed for use in the synthesis of the spongipyran macrolides. Functionalized dihydropyrans are transformed to cia tetrahydropyrans via a two step process: i) epoxidation using dimethyldioxirane and ii) Lewis acid mediated epoxide opening with allylstannanes as nucleophiles. This protocol, which can be successfully applied to complex systems, augments the limited body of methodology available for the preparation of beta-configured C-glycosides. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1709 / 1712

页数：4

共 16 条

[1] STEREOCONTROLLED SYNTHESIS OF C-GLYCOSIDES BY REACTION OF ORGANOCUPRATES WITH PROTECTED 1,2-ANHYDRO SUGARS, AND THEIR TRANSFORMATION INTO 2-DEOXY-C-GLYCOSIDES [J].

BELLOSTA, V ;

CZERNECKI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (03) :199-200

[2] The synthesis of some epoxyalkyl beta-C-glycosides as potential inhibitors of beta-glucan hydrolases [J].

Best, WM ;

Ferro, V ;

Harle, J ;

Stick, RV ;

Tilbrook, DMG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1997, 50 (05) :463-472

[3] Enantioselective synthesis of altohyrtin C (spongistatin 2):: Fragment assembly and revision of the spongistatin 2 stereochemical assignment [J].

Evans, DA ;

Trotter, BW ;

Côté, B ;

Coleman, PJ ;

Dias, LC ;

Tyler, AN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2744-2747

[4] ON THE DIRECT EPOXIDATION OF GLYCALS - APPLICATION OF A REITERATIVE STRATEGY FOR THE SYNTHESIS OF BETA-LINKED OLIGOSACCHARIDES [J].

HALCOMB, RL ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6661-6666

[5] SYNTHESIS OF TRANS-FUSED PERHYDROFUROPYRANS AND RELATED ALPHA-METHYLENE LACTONES - BICYCLIC RING-SYSTEMS PRESENT IN THE EZOMYCINS, THE OCTOSYL ACIDS, AND CERTAIN ANTI-TUMOR TERPENOIDS [J].

HANESSIAN, S ;

LIAK, TJ ;

DIXIT, DM .

CARBOHYDRATE RESEARCH, 1981, 88 (01) :C14-C19

[6] FURANOID GLYCAL AS A STARTING MATERIAL FOR NUCLEOSIDE DERIVATIVES [J].

KAWAKAMI, H ;

EBATA, T ;

KOSEKI, K ;

OKANO, K ;

MATSUMOTO, K ;

MATSUSHITA, H .

HETEROCYCLES, 1993, 36 (12) :2765-2776

[7]

KOBAYASHI M, 1993, CHEM PHARM BULL, V41, P989

[8]

Levy D.E., 1995, CHEM C GLYCOSIDES

[9]

LEWIS MD, 1982, J AM CHEM SOC, V104, P4796

[10] beta-selective C-glycosidations: Lewis-acid mediated reactions of carbohydrates with silyl ketene acetals [J].

Minehan, TG ;

Kishi, Y .

TETRAHEDRON LETTERS, 1997, 38 (39) :6815-6818

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