Chemistry of insect antifeedants from Azadirachta indica .21. Synthesis of model compounds of azadirachtin using a decalin framework as a functional group scaffolding

被引：11

作者：

delaPuente, ML

Ley, SV

Simmonds, MSJ

Blaney, WM

机构：

[1] UNIV CAMBRIDGE,DEPT CHEM,CAMBRIDGE CB2 1EW,ENGLAND

[2] ROYAL BOT GARDENS,JODRELL LAB,BIOL INTERACT SECT,BEHAV ENTOMOL GRP,RICHMOND TW9 3AB,SURREY,ENGLAND

[3] UNIV LONDON BIRKBECK COLL,BEHAV ENTOMOL GRP,LONDON,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 13期

关键词：

D O I：

10.1039/p19960001523

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An investigation has been carried out of the synthesis of structural models for the left hand portion of the natural product azadirachtin 1. This work has culminated in a concise and high-yielding route to decalin derivative 2. The significant antifeedant activity shown by this mimic 2 (AI(50) at 9.4 ppm) is greater than that of the other analogues synthesised during this study and has led to the synthesis of further mimics 3 and 4.

引用

页码：1523 / 1529

页数：7

共 19 条

[1] CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .10. SYNTHESIS OF A HIGHLY FUNCTIONALIZED DECALIN FRAGMENT OF AZADIRACHTIN
KOLB, HC
LEY, SV
TETRAHEDRON LETTERS, 1991, 32 (43) : 6187 - 6190
[2] CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA INDICA .4. SYNTHESIS TOWARDS THE LIMONOID AZADIRACHTIN - PREPARATION OF A FUNCTIONALIZED DECALIN FRAGMENT
LEY, SV
SOMOVILLA, AA
BROUGHTON, HB
CRAIG, D
SLAWIN, AMZ
TOOGOOD, PL
WILLIAMS, DJ
TETRAHEDRON, 1989, 45 (07) : 2143 - 2164
[3] Chemistry of insect antifeedants from Azadirachta indica (Part 22):: Functionalisation of the decalin fragment of azadirachtin via a Claisen rearrangement reaction
Ley, SV
Gutteridge, CE
Pape, AR
Spilling, CD
Zumbrunn, C
SYNLETT, 1999, (08) : 1295 - 1297
[4] CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .12. USE OF SILICON AS A CONTROL ELEMENT IN THE SYNTHESIS OF A HIGHLY FUNCTIONALIZED DECALIN FRAGMENT OF AZADIRACHTIN
KOLB, HC
LEY, SV
SLAWIN, AMZ
WILLIAMS, DJ
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (21): : 2735 - 2762
[5] CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .19. A POTENTIAL RELAY ROUTE FOR THE SYNTHESIS OF AZADIRACHTIN
DENHOLM, AA
JENNENS, L
LEY, SV
WOOD, A
TETRAHEDRON, 1995, 51 (23) : 6591 - 6604
[6] CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .18. DEMETHYLATION AND METHYLATION OF THE C-8 POSITION OF THE DECALIN PORTION OF AZADIRACHTIN
KOOT, WJ
LEY, SV
TETRAHEDRON, 1995, 51 (07) : 2077 - 2090
[7] CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .2. SYNTHESIS OF A POLYOXYGENATED DECALIN WITH LIMONOID STRUCTURAL HOMOLOGY
BRASCA, MG
BROUGHTON, HB
CRAIG, D
LEY, SV
SOMOVILLA, AA
TOOGOOD, PL
TETRAHEDRON LETTERS, 1988, 29 (15) : 1853 - 1856
[8] CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .14. ABSOLUTE-CONFIGURATION OF AZADIRACHTIN
LEY, SV
LOVELL, H
WILLIAMS, DJ
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (18) : 1304 - 1306
[9] CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .1. CONVERSION FROM THE AZADIRACHTIN TO THE AZADIRACHTININ SKELETONS
BILTON, JN
JONES, PS
LEY, SV
ROBINSON, NG
SHEPPARD, RN
TETRAHEDRON LETTERS, 1988, 29 (15) : 1849 - 1852
[10] CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .6. SYNTHESIS OF AN OPTICALLY PURE ACETAL INTERMEDIATE FOR POTENTIAL USE IN THE SYNTHESIS OF AZADIRACHTIN AND NOVEL ANTIFEEDANTS
ANDERSON, JC
LEY, SV
TETRAHEDRON LETTERS, 1990, 31 (03) : 431 - 432

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