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Syntheses of a prenylbisabolane diterpene, a natural insecticide from Croton linearis, and of the bisabolane sesquiterpenes (-)-delobanone and (-)-epi-delobanone
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
2002 (English)In: Tetrahedron, ISSN 0040-4020, Vol. 58, no 38, 7691-7700 p.Article in journal (Refereed) Published
Abstract [en]

An enantioselective first total synthesis of a constituent of Croton linearis, the (-)-7-hydroxy-3,10-prenylbisaboladien-2-one 1, is described as well as the syntheses of the 7-hydroxy-3,10-bisaboladien-2-ones (-)-epi-delobanone (14a) and (-)-delobanone (14b). The model compounds, 7-hydroxy-11-nor-methyl-3-bisabolen-2-one (8a), and 11,15-nor-dimethyl-7-hydroxy-3-bisabolen-2-one (8b), were successfully prepared by opening of the protected carvone epoxide derivative 6 with the appropriate organocuprates. An alternative approach was used for compounds 1 and 14. Thus, these were obtained from homogeranyllithium or homoprenyl Grignard reagent, which reacted successfully with a masked nor-carvone, ketone 11, prepared in four steps from (R)-carvone.

Place, publisher, year, edition, pages
2002. Vol. 58, no 38, 7691-7700 p.
Keyword [en]
Carvone enantioselctive synthesis Bisabolane
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-4067DOI: 10.1016/S0040-4020(02)00821-9ISI: 000178028700015Scopus ID: 2-s2.0-0037119801Local ID: 4589OAI: oai:DiVA.org:miun-4067DiVA: diva2:29099
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-10-25Bibliographically approved

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CiteExportLink to record
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Citation style
  • apa
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  • ieee
  • modern-language-association-8th-edition
  • vancouver
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More styles
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  • de-DE
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  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
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Output format
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  • asciidoc
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