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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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Synthesis of (±)-Pentalenene
✍ Shikai Zhao; Goverdan Mehta; Paul Helquist 📂 Article 📅 1991 🏛 Elsevier Science 🌐 French ⚖ 233 KB

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

Synthesis of (±)-pentalenene using elect
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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