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Erratum published on 20 March 2018, see Molecules 2018, 23(3), 704.
Open AccessArticle

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

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
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Author to whom correspondence should be addressed.
Molecules 2014, 19(12), 20664-20670; https://doi.org/10.3390/molecules191220664
Received: 13 October 2014 / Revised: 2 December 2014 / Accepted: 4 December 2014 / Published: 10 December 2014
(This article belongs to the Section Organic Chemistry)
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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MDPI and ACS Style

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

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