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

dc.contributor.author	Antonsen, Simen Gjelseth
dc.contributor.author	Skattebøl, Lars
dc.contributor.author	Stenstrøm, Yngve
dc.date.accessioned	2014-12-15T12:23:27Z
dc.date.accessioned	2014-12-16T10:16:11Z
dc.date.available	2014-12-15T12:23:27Z
dc.date.available	2014-12-16T10:16:11Z
dc.date.issued	2014
dc.identifier.citation	Molecules 2014, 19:20664-20670	nb_NO
dc.identifier.issn	1420-3049
dc.identifier.uri	http://hdl.handle.net/11250/227361
dc.description.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.	nb_NO
dc.language.iso	eng	nb_NO
dc.title	Synthesis of Racemic β-Chamigrene, a Spiro[5.5]undecane Sequiterpene	nb_NO
dc.type	Journal article	nb_NO
dc.type	Peer reviewed	nb_NO
dc.date.updated	2014-12-15T12:23:28Z
dc.identifier.doi	10.3390/molecules191220664
dc.identifier.cristin	1183604