TOTAL SYNTHESIS OF (+/-)-ALLOSAMIZOLINE FROM A SYMMETRICAL TRISUBSTITUTED CYCLOPENTENE

被引:36
作者
GOERING, BK [1 ]
GANEM, B [1 ]
机构
[1] CORNELL UNIV,BAKER LAB,DEPT CHEM,ITHACA,NY 14853
关键词
D O I
10.1016/0040-4039(94)88208-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convergent synthesis of the aminocyclitol allosamizoline 1, which is found in a class of pseudotrisaccharide chitinase inhibitors known as the allosamidins, is reported.
引用
收藏
页码:6997 / 7000
页数:4
相关论文
共 22 条
[1]   CYCLOHEXANE COMPOUNDS .V. REACTION OF 1-METHOXYCYCLOHEXENE-2 WITH AQUEOUS N-BROMOSUCCINIMIDE . 1-METHOXY-2-BROMO-3-HYDROXYCYCLOHEXANES [J].
BANNARD, RAB ;
CASSELMA.AA ;
HAWKINS, LR .
CANADIAN JOURNAL OF CHEMISTRY, 1965, 43 (08) :2398-&
[2]  
BELLUCCI G, 1973, TETRAHEDRON LETT, P3911
[3]   CHITIN SYNTHASE-1, AN AUXILIARY ENZYME FOR CHITIN SYNTHESIS IN SACCHAROMYCES-CEREVISIAE [J].
CABIB, E ;
SBURLATI, A ;
BOWERS, B ;
SILVERMAN, SJ .
JOURNAL OF CELL BIOLOGY, 1989, 108 (05) :1665-1672
[4]   SYNTHESIS OF SESQUITERPENE ANTI-TUMOR LACTONES .4. STEREOSELECTIVE SYNTHESIS OF TRANS-2,3-EPOXYCYCLOHEXANOL [J].
CHAVDARIAN, CG ;
HEATHCOCK, CH .
SYNTHETIC COMMUNICATIONS, 1976, 6 (04) :277-280
[5]   WHATS NEW IN CHITINASE RESEARCH [J].
FLACH, J ;
PILET, PE ;
JOLLES, P .
EXPERIENTIA, 1992, 48 (08) :701-716
[6]   TOTAL SYNTHESIS OF ALLOSAMIDIN - AN APPLICATION OF THE SULFONAMIDOGLYCOSYLATION OF GLYCALS [J].
GRIFFITH, DA ;
DANISHEFSKY, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (15) :5863-5864
[7]   SYNTHETIC STUDIES ON MANNOSTATIN-A AND ITS DERIVATIVES - A NEW FAMILY OF GLYCOPROTEIN PROCESSING INHIBITORS [J].
KING, SB ;
GANEM, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) :562-570
[8]   SYNTHETIC STUDIES ON ENZYME-INHIBITORS .2. SYNTHESIS OF (-)-ALLOSAMIZOLINE, THE PSEUDOAMINOSUGAR MOIETY OF ALLOSAMIDIN, A CHITINASE INHIBITOR [J].
KITAHARA, T ;
SUZUKI, N ;
KOSEKI, K ;
MORI, K .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1993, 57 (11) :1906-1909
[9]  
KNORR D, 1991, FOOD TECHNOL-CHICAGO, V45, P114
[10]  
LANGSTAF.EJ, 1967, CAN J CHEMISTRY, V45, P1907