Synthetic studies towards bridgehead diprenyl-substituted bicyclo[3.3.1]nonane-2,9-diones as models for polyprenylated acylphloroglucinol construction

Journal article

The synthesis of bridgehead diprenylated bicyclo[3.3.1]-nonane-2,9-dione, based on a reductive rearrangement of an enol lactone, is presented. The same target could be reached by a one-step sequence involving Michael addition of 2,6-diprenylcyclohexanone onto acrolein and intramolecular aldol reaction. The first method could be extended to the formation of a compound with gem-dimethyl substituents adjacent to the bridgehead position, but the construction of a suitably substituted enol lactone, with a view to polyprenylated acylphloroglucinol elaboration, could not be achieved. © Wiley-VCH Verlag GmbH and Co. KGaA, 2007.

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

• Publication status: Published
• Journal: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
• Volume: 2007
• Issue: 30
• Pages: 5117-5125
• Publication date: 2007-10-01
• DOI: 10.1002/ejoc.200700430
• EISSN: 1099-0690
• ISSN: 1434-193X
• Language: English
• Keywords: reduction; rearrangement; Michael addition; aldol reactions; acylphloroglucinols; enol lactones