Synthesis of active antifeedant CDE fragments of 11-ketoepoxyazadiradione based on an electrocyclization reaction catalyzed by perchloric acid

Authors
Fernandez-Mateos, A de la Nava, EMM Coca, GP Gonzalez, RR Silvo, AIR Simmonds, MSJ Blaney, WM
Citation
A. Fernandez-mateos et al., Synthesis of active antifeedant CDE fragments of 11-ketoepoxyazadiradione based on an electrocyclization reaction catalyzed by perchloric acid, J ORG CHEM, 63(25), 1998, pp. 9440-9447
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
63
Issue
25
Year of publication
1998
Pages
9440 - 9447
Database
ISI
SICI code
0022-3263(199812)63:25<9440:SOAACF>2.0.ZU;2-A
Abstract
A synthetic route to mimics of the insect antifeedant epoxyazadiradione con taining the CDE molecular fragment with an oxygenated function on ring C ha s been developed. The key step is based on a 2,6-diene-1,5-dione electrocyc lization reaction catalyzed by perchloric acid, The rearrangement of the ep oxy alcohol epimers 12 and 19 induced by acids deserves special mention. Se veral of the compounds obtained show significant antifeedant activity again st Spodoptera frugiperda.