A stereoselective synthesis of (+/-)-C-secolimonoid BCDE model compounds related to the insect antifeedant ohchinolide.
A short and stereoselective synthesis of a (+/-)-BCDE C-secolimonid model insect antifeedant related to ohchinolide and nimbolidin was accomplished in 13 (30% overall yield) and 15 (30% overall yield) steps, respectively, from ethyl drimanate. The key steps are the torquoselective electrocyclization of the divinyl ketone 6, induced by perchloric acid, and the stereoselective rearrangement of the hydroxy lactone 12, inspired in a biosynthetic proposal. An alternative route, which provides access to (+/-)-BCDE ohchinolide and nimbolidin isomers, is also described.
Mateos
A F
AF
Universidad de Salamanca, Facultad de C. Químicas, Departamento de Química Orgánica, Plaza de los Caídos 1-5, 37008 Salamanca, Spain. afmateos@gugu.usal.es
Martín de la Nava
E M
EM
González
R R
RR
D000818:Animals; D003521:Cyclopropanes / Q000138:chemical synthesis*; D005247:Feeding Behavior / Q000187:drug effects; D007313:Insecta / Q000187:drug effects*; D007306:Insecticides / Q000138:chemical synthesis* / Q000494:pharmacology; D007814:Larva / Q000187:drug effects; D010944:Plants; D011714:Pyrans / Q000138:chemical synthesis*; D018411:Spodoptera / Q000187:drug effects; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
D003521:Cyclopropanes; D007306:Insecticides; D011714:Pyrans; D014315:Triterpenes; C444260:plagiochiline N