TOTAL SYNTHESIS OF NOVEL CONDURITOL RELATED-COMPOUNDS CAPABLE OF MODULATING INSULIN RELEASE

被引：44

作者：

BILLINGTON, DC ^{[1
]}

PERRONSIERRA, F ^{[1
]}

PICARD, I ^{[1
]}

BEAUBRAS, S ^{[1
]}

DUHAULT, J ^{[1
]}

ESPINAL, J ^{[1
]}

CHALLAL, S ^{[1
]}

机构：

[1] INST RECH SERVIER,DEPT METAB DIS,F-92150 SURESNES,FRANCE

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1994年 / 4卷 / 19期

关键词：

D O I：

10.1016/0960-894X(94)85030-5

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The syntheses of the six isomeric conduritols A - F, and of a series of bicyclic and tricyclic polyols related to the conduritols are described. Conduritols A and B, and representative analogues are able to modulate the release of insulin from isolated pancreatic islets in the presence of varying concentrations of glucose, in both a stimulatory and an inhibitory sense.

引用

页码：2307 / 2312

页数：6

共 22 条

[1] SYNTHESIS OF (-)-CONDURITOL F, (+)-CONDURITOL-B, CYCLOPHELLITOL FROM L-QUEBRACHITOL [J].

AKIYAMA, T ;

SHIMA, H ;

OHNARI, M ;

OKAZAKI, T ;

OZAKI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (12) :3760-3767

[2] BENZENE DIOL EPOXIDES [J].

ALEKSEJCZYK, RA ;

BERCHTOLD, GA ;

BRAUN, AG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (08) :2554-2555

[3] CONDURITOLS AND RELATED-COMPOUNDS [J].

BALCI, M ;

SUTBEYAZ, Y ;

SECEN, H .

TETRAHEDRON, 1990, 46 (11) :3715-3742

[4] SYNTHESES OF CONDURITOL-D DERIVATIVES FROM AROMATIC-COMPOUNDS [J].

CARLESS, HAJ ;

BUSIA, K ;

DOVE, Y ;

MALIK, SS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (21) :2505-2506

[5] ENANTIOSPECIFIC AND STEREOSELECTIVE SYNTHESIS OF (-)-CONDURITOL-C FROM CHLOROBENZENE VIA MICROBIAL OXIDATION AND EPOXIDATION [J].

CARLESS, HAJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (03) :234-235

[6]

CARLESS HAJ, 1992, TETRAHEDRON-ASYMMETR, V3, P75

[7] DARSTELLUNG VON KONDURIT-D DURCH DIENSYNTHESE [J].

CRIEGEE, R ;

BECHER, P .

CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (11) :2516-2521

[8]

Day C., 1990, NEW ANTIDIABETIC DRU, P267

[9] MICROBIAL OXIDATION OF AROMATICS IN ENANTIOCONTROLLED SYNTHESIS .2. RATIONAL DESIGN OF AZA SUGARS (ENDO-NITROGENOUS) - TOTAL SYNTHESIS OF (+)-KIFUNENSINE, MANNOJIRIMYCIN, AND OTHER GLYCOSIDASE INHIBITORS [J].

HUDLICKY, T ;

ROUDEN, J ;

LUNA, H ;

ALLEN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5099-5107

[10] MICROBIAL OXIDATION OF AROMATICS IN ENANTIOCONTROLLED SYNTHESIS .3. DESIGN OF AMINO CYCLITOLS (EXO-NITROGENOUS) AND TOTAL SYNTHESIS OF (+)-LYCORICIDINE VIA ACYLNITROSYL CYCLOADDITION TO POLARIZED 1-HALO-1,3-CYCLOHEXADIENES [J].

HUDLICKY, T ;

OLIVO, HF ;

MCKIBBEN, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5108-5115

← 1 2 3 →