Alpha,alpha'-annulation of 2,6-prenyl-substituted cyclohexanone derivatives with malonyl chloride: application to a short synthesis of (+/-)-clusianone. Formation and rearrangement of a biogenetic-like intermediate.

Journal article

Conditions were found for the successful Effenberger alpha,alpha'-annulation of 3,3-dimethyl-2,4,6-triprenyl cyclohexanone silyl enol ethers with malonyl chloride to give the corresponding bicyclo[3.3.1]nonane-trione in 35% yield, this result allowing a short synthesis of (+/-)-clusianone. An isomeric rearranged bicyclo[3.3.1]nonane-trione was also isolated in 25% yield, and changing the Lewis acid resulted in formation of a lavandulyl-substituted phloroglucinol derivative in 38% yield. The m...

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Authors: Nuhant, P; David, M; Pouplin, T; Delpech, B; Marazano, C

• Publication status: Published
• Journal: Organic letters
• Volume: 9
• Issue: 2
• Pages: 287-289
• Publication date: 2007-01-01
• DOI: 10.1021/ol062736s
• EISSN: 1523-7052
• ISSN: 1523-7060
• Language: English
• Keywords: Hydrocarbons, Chlorinated; Cyclohexanones; Bicyclo Compounds; Biomimetic Materials; Molecular Structure; Stereoisomerism