Issue 20, 1999
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Rearrangement approaches to sesquiterpenes containing multiple contiguous quaternary carbon atoms. Total synthesis of (±)-myltayl-8(12)-ene and (±)-6-epijunicedranol

A. Srikrishna,   C. V. Yelamaggad  and  P. Praveen Kumar  

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).

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Article information

DOI
https://doi.org/10.1039/A906706J
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1999, 2877-2881

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Rearrangement approaches to sesquiterpenes containing multiple contiguous quaternary carbon atoms. Total synthesis of (±)-myltayl-8(12)-ene and (±)-6-epijunicedranol

A. Srikrishna, C. V. Yelamaggad and P. Praveen Kumar, J. Chem. Soc., Perkin Trans. 1, 1999, 2877 DOI: 10.1039/A906706J

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