CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .19. A POTENTIAL RELAY ROUTE FOR THE SYNTHESIS OF AZADIRACHTIN

被引:39
作者
DENHOLM, AA
JENNENS, L
LEY, SV
WOOD, A
机构
[1] UNIV CAMBRIDGE,DEPT CHEM,CAMBRIDGE CB2 1EW,ENGLAND
[2] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND
关键词
D O I
10.1016/0040-4020(95)00297-L
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A potential relay route for the synthesis of azadirachtin (1) has been established. An advanced intermediate 4 has been prepared and methods to convert this back to the natural product have been developed, in particular, the reintroduction of the enol double bond using an acetal exchange process.
引用
收藏
页码:6591 / 6604
页数:14
相关论文
共 24 条
[1]   CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .7. PREPARATION OF AN OPTICALLY PURE HYDROXYACETAL EPOXIDE RELATED TO AZADIRACHTIN [J].
ANDERSON, JC ;
LEY, SV .
TETRAHEDRON LETTERS, 1990, 31 (24) :3437-3440
[2]   CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .8. SYNTHESIS OF HYDROXYDIHYDROFURAN ACETAL FRAGMENTS FOR BIOLOGICAL EVALUATION AND AZADIRACHTIN TOTAL SYNTHESIS STUDIES [J].
ANDERSON, JC ;
LEY, SV ;
SANTAFIANOS, D ;
SHEPPARD, RN .
TETRAHEDRON, 1991, 47 (33) :6813-6850
[3]  
ANDERSON JC, 1990, THESIS IMPERIAL COLL
[4]  
BLANEY WM, IN PRESS ENTOMOL EXP
[5]  
BROUGHTON HB, 1985, J CHEM SOC CHEM COMM, P46
[6]  
BUTTERWORTH JH, 1968, J CHEM SOC CHEM COMM, P23
[7]   BIS(BOC) AMINO-ACID FLUORIDES AS REACTIVE PEPTIDE COUPLING REAGENTS [J].
CARPINO, LA ;
MANSOUR, ESME ;
EL-FAHAM, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :4162-4164
[8]  
CHENG YS, 1980, SYNTHESIS-STUTTGART, P223
[9]  
DENHOLM AA, UNPUB
[10]  
ELLENBERGER WP, 1993, Patent No. 5229007