A stereoselective synthesis of (+/-)-C-secolimonoid BCDE model compounds related to the insect antifeedant ohchinolide

Authors
Mateos, AF de la Nava, EMM Gonzalez, RR
Citation
Af. Mateos et al., A stereoselective synthesis of (+/-)-C-secolimonoid BCDE model compounds related to the insect antifeedant ohchinolide, J ORG CHEM, 66(23), 2001, pp. 7632-7638
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
23
Year of publication
2001
Pages
7632 - 7638
Database
ISI
SICI code
0022-3263(20011116)66:23<7632:ASSO(B>2.0.ZU;2-T
Abstract
A short and stereoselective synthesis of a (+/-)-BCDE C-secolimonid model i nsect antifeedant related to ohchinolide and nimbolidin was accomplished in 13 (30% overall yield) and 15 (30% overall yield) steps, respectively, fro m ethyl drimanate. The key steps are the torquoselective electrocyclization of the divinyl ketone 6, induced by perchloric acid, and the stereoselecti ve rearrangement of the hydroxy lactone 12, inspired in a biosynthetic prop osal. An alternative route, which provides access to (+/-)-BCDE ohchinolide and nimbolidin isomers, is also described.