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Molecules 2014, 19(12), 20664-20670; doi:10.3390/molecules191220664

Synthesis of Racemic β-Chamigrene, a Spiro[5.5]undecane Sequiterpene

1
IKBM, P.O. Box 5003, NMBU, The Norwegian University of Life Sciences, N-1430 Ås, Norway
2
Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern, N-0315 Oslo, Norway
*
Author to whom correspondence should be addressed.
Received: 13 October 2014 / Revised: 2 December 2014 / Accepted: 4 December 2014 / Published: 10 December 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

The present paper describes a total synthesis of racemic β-chamigrene (1), a sesquiterpene with a spiro[5.5]undecane carbon framework. Compared with previously reported β-chamigrene syntheses, we were able to reduce the total number of reaction steps, which also resulted in a significant improvement of the overall yield. The commercially available ketone 6-methylhept-5-en-2-one was transformed by known simple procedures into 3,3-dimethyl-2-methylenecyclohexanone. This reacted with isoprene by a Diels-Alder reaction to give a spiro ketone. An olefination reaction on this compound gave the target molecule. View Full-Text
Keywords: natural product; sesquiterpene; β-chamigrene; Diels-Alder; microwave synthesis; spiro[5.5]undecane natural product; sesquiterpene; β-chamigrene; Diels-Alder; microwave synthesis; spiro[5.5]undecane
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Antonsen, S.; Skattebøl, L.; Stenstrøm, Y. Synthesis of Racemic β-Chamigrene, a Spiro[5.5]undecane Sequiterpene. Molecules 2014, 19, 20664-20670.

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