Proceedings of the Symposium on Progress in Organic Reactions and Syntheses
37th Symposium on Progress in Organic Reactions and Syntheses
Session ID : 1P-45
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An efficient method for C-prenylation of flavonoid and its application to the synthesis of related compounds
*Tomoyuki KawamuraMoemi HayashiRie MukaiJunji TeraoHisao Nemoto
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Abstract
Flavonoids are plant secondary metabolites and have various biological activities. Additionally, more attractive bioactivities of the prenylated derivatives than those of original flavonoids have been frequently discovered. Therefore, development of the efficient and general prenylating procedure of flavonoids was desirable. We report here an efficient method for C-prenylation of flavonoids, and their evaluation of suppressive effect on disused muscular atrophy based on our recent report. Our procedure for prenylation of flavonoids is selective protection and/or deprotection of hydroxyl groups, palladium-catalyzed O-1,1-dimethyl-2-propenylation and the following regioselective Claisen rearrangement for the carbon-carbon bond formation as the key steps.
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© 2011 The Pharmaceutical Society of Japan
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