A biomimetic approach to C-secolimonoids: Synthesis of CDE ohchinolide andnimbolidin model compounds

Authors
Mateos, AF de la Nava, EM Gonzalez, RR
Citation
Af. Mateos et al., A biomimetic approach to C-secolimonoids: Synthesis of CDE ohchinolide andnimbolidin model compounds, SYNLETT, (9), 2001, pp. 1399-1402
Citations number
8
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
9
Year of publication
2001
Pages
1399 - 1402
Database
ISI
SICI code
0936-5214(200109):9<1399:ABATCS>2.0.ZU;2-R
Abstract
A concise and stereoselective synthesis of CDE ohchinolide and nimbolidin m odel compounds has been accomplished in ten and twelve steps respectively f rom alpha -cyclocitral, in 30% overall yield. The key step is a biomimetic type of allylic rearrangement induced by thionyl chloride. A potent insect antifeedant activity was found for two of the model compounds synthesised.