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Synlett 1998; 1998(12): 1372-1374
DOI: 10.1055/s-1998-1962
DOI: 10.1055/s-1998-1962
letter
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Synthesis of C-seco Limonoid Model Insect Antifeedants Related to Ochinolide
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
![](https://www.thieme-connect.de/media/synlett/199812/lookinside/thumbnails/10.1055-s-1998-1962-1.jpg)
A short and selective synthesis of C-seco limonoid model insect antifeedant related to ochinolide was accomplished in seven steps from α-cyclocitral. The key steps are the electrocyclization of a β-acyl divinyl ketone induced by perchloric acid, and a selective retroclaisen reaction. A rare example of atropisomerism was found in the trisubstituted cyclopentenone 6 key intermediate.
Nazarov reaction - retroclaisen reaction - perchloric acid - antifeedant - limonoids