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Total synthesis of (±)-Δ9(12)-capnellene

✍ Scribed by H.J. Liu; M.G. Kulkarni


Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
253 KB
Volume
26
Category
Article
ISSN
0040-4039

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Stereocontrolled total synthesis of (±)-
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The first total synthesis of the marine triquinane sesquiterpene Δ9(12)-capnellene ( 1 ) is described.

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## Abstract The synthesis of the (±)‐form of the marine sesquiterpene (–)‐Δ^9(12)^‐capnellene (**1**) by double application of the __a__‐alkynone cyclization is described. Starting with 2, 2, 5‐trim ethylcyclopentanone (**2**), the elaboration of the tricyclo [6.3.0.0^2,6^]undecane C‐skeleton of **

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✍ Wolfgang Oppolzer; Kurt Bättig 📂 Article 📅 1982 🏛 Elsevier Science 🌐 French ⚖ 224 KB

The marine triquinane sesquiterpene A 9(12) -capnellene (1) was synthesised from 2,2,5-trimethyl-5-hexenal (2) by a sequence of 11 synthetic operations \_ in 5% overall yield. The key steps 3 + 4 + 5 -f 6 involve two intramolecular type-I-"Mg-ene" processes.