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Synthesis of the angular triquinane (±)-pentalenene via small ring intermediates.

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

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
266 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis

Dimethyl t-butylsilyl enol ethers of cycloalkananes react with ethyl propynoore in the presence of ZrCl4 to give protected cyclobutenic hydroxy esters. Cycloproponation by cycloaddition of diazoalkanes followed by sensitized photocleavage. leads to bicycle I2.1 .O] pentan-2-ol derivatives which are then cleaved with acids to 3-cyclopenten-l-ok This reaction sequence was used for the synthesis of the angular triquinane (fj-pentalenene. starting from 3,3dimethylcyclopentan and diazoethane (+ ring A and BJ, the ring C being obtuined by a silyl-assisted Nazarov type cyclization.

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Synthesis of small rings via the protect
Synthesis of small rings via the protected cyanohydrin method.
✍ Gilbert Stork; Jean Claude Depezay; Jean d'Angelo 📂 Article 📅 1975 🏛 Elsevier Science 🌐 French ⚖ 208 KB

We have reported that the anion derived from the readily available protected cyanohydrins of aldehydes are generally useful as acyl carbanion equivalents and can be used in the synthesis of ketones v&, inter alia, alkylation and --Michael addition.