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