Synthetic Studies Towards Bridgehead Diprenyl‐Substituted Bicyclo[3.3.1]nonane‐2,9‐diones as Models for Polyprenylated Acylphloroglucinol Construction

Author:

Pouplin Thomas,Tolon Blanca,Nuhant Philippe,Delpech Bernard,Marazano Christian

Abstract

AbstractThe 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 & Co. KGaA, 69451 Weinheim, Germany, 2007)

Publisher

Wiley

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