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The cyclobutenic way to triquinanes. Synthesis of (±) silphinene

✍ Scribed by Michel Franck-Neumann; Michel Miesch; Laurence Gross

Book ID
104212846
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
150 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

The easily accessible alcohol 2 is oxidized. after protection, to the allylic alcohol 3. The bensyl ether of this diquinonic alcohol is tran&omted into the tn~quinanic precursor 9 of(+) Silphinene, wing a similar reaction sequence as described previously, but using the opposite epimer.

📜 SIMILAR VOLUMES

Total Synthesis of (±)-Silphinene: non p
Total Synthesis of (±)-Silphinene: non photochemical cyclobutenic route to a crucial intermediate
✍ Michel Miesch; Laurence Miesch-Gross; Michel Franck-Neumann 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 432 KB

The cyclobutenic ester 1, readily available by thermal [2+2] cycloaddition of the silyl enol ether derived from cyclopentanone with ethyl propynoate, is easily transformed into the diquinanic alcohol 3 via the bicyclo [2.1.0] pentane intermediate 2. After protection as the thexyldimethylsilyl ether,