SYNTHESIS OF (-)-CONDURITOL F, (+)-CONDURITOL-B, CYCLOPHELLITOL FROM L-QUEBRACHITOL

被引：37

作者：

AKIYAMA, T

SHIMA, H

OHNARI, M

OKAZAKI, T

OZAKI, S

机构：

[1] Department of Applied Chemistry, Faculty of Engineering, Ehime University, Bunkyo-cho

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1993年 / 66卷 / 12期

关键词：

D O I：

10.1246/bcsj.66.3760

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The methyl ether of cyclitols with vicinal hydroxyl group was cleaved chemoselectively in preference to both cis- and trans-cyclohexylidene moieties by AlCl3-n-Bu4NI to afford parent alcohols in good yields. (-)-Conduritol F was prepared from L-quebrachitol, an optically active cyclitol from the serum of rubber trees, in five steps by use of the demethylation reaction. The first chiral synthesis of (+)-conduritol B and the total synthesis of cyclophellitol, a novel beta-glucosidase inhibitor, are described.

引用

页码：3760 / 3767

页数：8

共 67 条

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[4] DIASTEREOSELECTIVE REDUCTION OF ALPHA-KETO ESTERS BEARING CHIRO-INOSITOL DERIVATIVES AS CHIRAL AUXILIARIES
AKIYAMA, T
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[6] A CHIRAL SYNTHESIS OF D-MYO-INOSITOL 1-PHOSPHATE STARTING FROM L-QUEBRACHITOL
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[8] A CONCISE SYNTHESIS OF (-)-CONDURITOL-F FROM L-QUEBRACHITOL VIA ALCL3-NORMAL-BU4NI MEDIATED DEMETHYLATION
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