A short, formal synthesis is reported for pentalenene. The key steps are copper-catalyzed 1,4-addition of isobutylmagnesium bromide to a cyclooctenone derivative, enolate alkylation with the thiocarbene complex [(@-C5H5)(CO)2Fe=CHSPh]+ PFg-, and cyclopentane ring formation by means of intramolecular
✦ LIBER ✦
Synthesis of (±)-pentalenene
✍ Scribed by Gerald Pattenden; Simon J. Teague
- Book ID
- 104233721
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- French
- Weight
- 216 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A total synthesis of (+)-pentalenene cl), based on transannulation of the bicycloB.3.0] undecadiene (15) in the presence of boron trifluoride etherate, is described.
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lldione. whichhas been produced efficiently by means of electrochemical method. Pentalenene belongs to a group of triquinane sesquiterpenesl and is attractive to synthetic chemists.2f We describe herein a synthesis of (f)-pentalenene u&g electrochemical method as a key step. The known phenol (1) (4