Stereocontrolled total synthesis of (±)-Δ9(12)-capnellene
✍ Scribed by Kenneth E. Stevens; Leo A. Paquette
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 255 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The first total synthesis of the marine triquinane sesquiterpene Δ9(12)-capnellene (
1
) is described.
📜 SIMILAR VOLUMES
A novel, efficient and stefeosp~ific synthesis of(\_+) capnellene fi'om p-ca-esol is reported.
## 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 **
A direct stereocontrolled route for the construction of highly substituted cyclopentanones 10a-d has been developed starting from aeyclic ketones 5a,b. The key step involves copper(I)-eatalysed stezeoselective photocycloaddition of the dienes 6a-d followed by stereospecific rearrangement of the cycl