A NOVEL STEREO-CONTROLLED AND REGIO-CONTROLLED SYNTHESIS OF 2-DEOXY-ALPHA-O-ARYL GLUCOSIDES

被引：5

作者：

CAPOZZI, G

FALCIANI, C

MENICHETTI, S

NATIVI, C

FRANCK, RW

机构：

[1] UNIV FLORENCE,DIPARTIMENTO CHIM ORGAN,CNR,CTR CHIM & STRUTTURA COMPOSTI ETEROCICLICI,I-50121 FLORENCE,ITALY

[2] CUNY HUNTER COLL,DEPT CHEM,NEW YORK,NY 10021

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 37期

关键词：

D O I：

10.1016/00404-0399(50)1333-D

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The totally regio- and highly stereo-selective [4+2] cycloaddition of ortho-thioquinones 2a and 2b to substituted-D-glucals 3 represents a new and effective tool for the synthesis of 2-deoxy-alpha-O-aryl glucosides.

引用

页码：6755 / 6758

页数：4

共 28 条

[1] DIRECT PREPARATION OF 2-DEOXY-D-GLUCOPYRANOSIDES FROM GLUCALS WITHOUT FERRIER REARRANGEMENT [J].

BOLITT, V ;

MIOSKOWSKI, C ;

LEE, SG ;

FALCK, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5812-5813

[2] PHTHALIMIDESULFENYL CHLORIDE .8. REACTION WITH ACTIVATED ARENES - THE FIRST EXAMPLE OF ORTHO-THIOQUINONES GENERATION [J].

CAPOZZI, G ;

MENICHETTI, S ;

NATIVI, C ;

SIMONTI, MC .

TETRAHEDRON LETTERS, 1994, 35 (50) :9451-9454

[3] PHTHALIMIDESULFENYL CHLORIDE .6. THE 1ST EXAMPLE OF AN ALPHA-OXOTHIONE ACTING AS HETERODIENE - SYNTHESIS OF 2,3-DIHYDRO-1,4-OXATHIINES [J].

CAPOZZI, G ;

NATIVI, C ;

ROSI, A ;

FRANCK, RW ;

MENICHETTI, S .

TETRAHEDRON LETTERS, 1993, 34 (26) :4253-4256

[4] POLARIZED-PI FRONTIER MOLECULAR-ORBITAL (PPFMO) AND EXPERIMENTAL STUDIES OF FACIAL SELECTIVITY IN ELECTROPHILIC ATTACKS ON SUBSTITUTED ALKENES [J].

FRANCK, RW ;

KAILA, N ;

BLUMENSTEIN, M ;

GEER, A ;

HUANG, XL ;

DANNENBERG, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5335-5337

[5]

FRANCK RW, 1989, STUDIES NATURAL PROD, P173

[6] ARYLBIS(ARYLTHIO)SULFONIUM SALTS AS REAGENTS FOR THE SYNTHESIS OF 2-DEOXY-BETA-GLYCOSIDES [J].

GREWAL, G ;

KAILA, N ;

FRANCK, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2084-2092

[7] SULFONAMIDOGLYCOSYLATION OF GLYCALS - A ROUTE TO OLIGOSACCHARIDES WITH 2-AMINOHEXOSE SUBUNITS [J].

GRIFFITH, DA ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (15) :5811-5819

[8] THE TOTAL SYNTHESIS OF (-)-CRYPTOSPORIN [J].

GUPTA, RB ;

FRANCK, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7668-7670

[9] FIRST TOTAL SYNTHESIS OF BE-12406-A [J].

HOSOYA, T ;

TAKASHIRO, E ;

MATSUMOTO, T ;

SUZUKI, K .

TETRAHEDRON LETTERS, 1994, 35 (26) :4591-4594

[10] NOVEL APPROACHES TO GLYCOSIDE SYNTHESIS - SULFENATE ESTERS AS GLYCOSYL ACCEPTORS - A NOVEL-APPROACH TO THE SYNTHESIS OF 2-DEOXYGLYCOSIDES [J].

ITO, Y ;

OGAWA, T .

TETRAHEDRON LETTERS, 1987, 28 (24) :2723-2726

← 1 2 3 →