Srikrishna, A. ; Yelamaggad, C. V. ; Praveen Kumar, P. (1999) Rearrangement approaches to sesquiterpenes containing multiple contiguous quaternary carbon atoms. Total synthesis of (±)-myltayl-8(12)-ene and (±)-6-epijunicedranol Journal of the Chemical Society, Perkin Transactions 1 (20). pp. 2877-2881. ISSN 0300-922X
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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1999...
Related URL: http://dx.doi.org/10.1039/A906706J
Abstract
Details of the first total syntheses of the sesquiterpenes myltayl-8(12)-ene and 6-epijunicedran-8-ol are described. The aldehyde 13, obtained by Claisen rearrangement of cyclogeraniol, was transformed into the dienones 12 and 18. Boron trifluoride-diethyl ether mediated cyclization and rearrangement transformed the dienones 12 and 18 into the tricyclic ketones 16 and 17, efficiently creating three and four contiguous quaternary carbon atoms, respectively. Wittig methylenation of 16 furnished (±)-myltayl-8(12)-ene (11), whereas reduction of the ketone 17 furnished (±)-6-epijunicedranol (23).
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 48826 |
| Deposited On: | 15 Jul 2011 12:29 |
| Last Modified: | 15 Jul 2011 12:29 |
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