TOTAL SYNTHESIS OF (-)-ALLOSAMIDIN, AN INSECT CHITINASE INHIBITOR, EMPLOYING CHITIN AS A KEY STARTING MATERIAL

被引：42

作者：

TAKAHASHI, S ^{[1
]}

TERAYAMA, H ^{[1
]}

KUZUHARA, H ^{[1
]}

机构：

[1] INST PHYS & CHEM RES,WAKO,SAITAMA 35101,JAPAN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(00)60825-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-Allosamidin (1), a novel insect chitinase inhibitor, was stereoselectively synthesized from di- and monosaccharidic constituents of chitin, N,N'-diacetylchitobiose (2) and D-glucosamine (3).

引用

页码：7565 / 7568

页数：4

共 18 条

[11] SEARCH FOR MICROBIAL INSECT GROWTH-REGULATORS .2. ALLOSAMIDIN, A NOVEL INSECT CHITINASE INHIBITOR [J].

SAKUDA, S ;

ISOGAI, A ;

MATSUMOTO, S ;

SUZUKI, A .

JOURNAL OF ANTIBIOTICS, 1987, 40 (03) :296-300

[12] THE STRUCTURE OF ALLOSAMIDIN, A NOVEL INSECT CHITINASE INHIBITOR, PRODUCED BY STREPTOMYCES SP [J].

SAKUDA, S ;

ISOGAI, A ;

MATSUMOTO, S ;

SUZUKI, A ;

KOSEKI, K .

TETRAHEDRON LETTERS, 1986, 27 (22) :2475-2478

[13] STEREOCONTROLLED SYNTHESIS OF (-)-ALLOSAMIZOLINE USING D-GLUCOSAMINE AS A CHIRAL TEMPLATE [J].

TAKAHASHI, S ;

TERAYAMA, H ;

KUZUHARA, H .

TETRAHEDRON LETTERS, 1991, 32 (38) :5123-5126

[14]

TERAYAMA H, UNPUB J CARBOHYDR CH

[15] PERACETYLATED LAMINARIBIOSE - PREPARATION BY SPECIFIC DEGRADATION OF CURDLAN AND ITS CHEMICAL CONVERSION INTO N-ACETYLHYALOBIURONIC ACID [J].

WANG, LX ;

SAKAIRI, N ;

KUZUHARA, H .

CARBOHYDRATE RESEARCH, 1991, 219 :133-148

[16] ACID-CATALYZED BENZYLATION AND ALLYLATION BY ALKYL TRICHLOROACETIMIDATES [J].

WESSEL, HP ;

IVERSEN, T ;

BUNDLE, DR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2247-2250

[17] 5-MEMBERED RINGS .2. INTER AND INTRAMOLECULAR REACTIONS OF SIMPLE AMINES WITH N-SUBSTITUTED PHTHALIMIDES - METHYLAMINE AS A REAGENT FOR REMOVAL OF A PHTHALOYL GROUP FROM NITROGEN [J].

WOLFE, S ;

HASAN, SK .

CANADIAN JOURNAL OF CHEMISTRY, 1970, 48 (22) :3572-&

[18] BIOSYNTHETIC-STUDIES ON THE CHITINASE INHIBITOR, ALLOSAMIDIN - ORIGIN OF THE CARBON AND NITROGEN-ATOMS [J].

ZHOU, ZY ;

SAKUDA, S ;

YAMADA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (13) :1649-1652

← 1 2 →