Synthesis of Quinolactacide via an Acyl Migration Reaction and Dehydrogenation with Manganese Dioxide, and Its Insecticidal Activities.
- Resource Type
- Article
- Authors
- Abe, Masaki; Imai, Tetsuya; Ishii, Naoki; Usui, Makio
- Source
- Bioscience, Biotechnology & Biochemistry. Jan2006, Vol. 70 Issue 1, p303-306. 4p.
- Subject
- *PENICILLIUM
*ACETONE
*HYDROGENATION
*COAL liquefaction
*RING formation (Chemistry)
- Language
- ISSN
- 0916-8451
The article presents a synthetic study on quinolactacide to obtain a sufficient amount of the compound. Quinolactacide isolated from Penicillium citrinium F 1539 which was synthesized and evaluated for its insecticidal activities. Acyl migration of 11 catalyzed with acetone cynahohydrin proceeded quantitatively to give trione 12. Hydrogenation of the nitro group of trione 12 resulted in spontaneous cyclization to give tetrahydroquinolactacide 13 in a 52 percent yield.