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

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...

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Detalles Bibliográficos
Autores principales: Antonsen, Simen, Skattebøl, Lars, Stenstrøm, Yngve
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271544/
https://www.ncbi.nlm.nih.gov/pubmed/25514056
http://dx.doi.org/10.3390/molecules191220664
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author Antonsen, Simen
Skattebøl, Lars
Stenstrøm, Yngve
author_facet Antonsen, Simen
Skattebøl, Lars
Stenstrøm, Yngve
author_sort Antonsen, Simen
collection PubMed
description 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.
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spelling pubmed-62715442018-12-28 Synthesis of Racemic β-Chamigrene, a Spiro[5.5]undecane Sesquiterpene Antonsen, Simen Skattebøl, Lars Stenstrøm, Yngve Molecules Article 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. MDPI 2014-12-10 /pmc/articles/PMC6271544/ /pubmed/25514056 http://dx.doi.org/10.3390/molecules191220664 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Antonsen, Simen
Skattebøl, Lars
Stenstrøm, Yngve
Synthesis of Racemic β-Chamigrene, a Spiro[5.5]undecane Sesquiterpene
title Synthesis of Racemic β-Chamigrene, a Spiro[5.5]undecane Sesquiterpene
title_full Synthesis of Racemic β-Chamigrene, a Spiro[5.5]undecane Sesquiterpene
title_fullStr Synthesis of Racemic β-Chamigrene, a Spiro[5.5]undecane Sesquiterpene
title_full_unstemmed Synthesis of Racemic β-Chamigrene, a Spiro[5.5]undecane Sesquiterpene
title_short Synthesis of Racemic β-Chamigrene, a Spiro[5.5]undecane Sesquiterpene
title_sort synthesis of racemic β-chamigrene, a spiro[5.5]undecane sesquiterpene
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271544/
https://www.ncbi.nlm.nih.gov/pubmed/25514056
http://dx.doi.org/10.3390/molecules191220664
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