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Paper | Regular issue | Vol 43, No. 2, 1996, pp.277-285
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7078
Total Synthesis of 8-(1,1-Dimethylallyl)apigenin

Hélène Raguenet, Denis Barron,* and Anne-Marie Mariotte

*Pharmacognosy Laboratory, School of Pharmacy, Joseph-Fourier University-Grenoble I, 38706 La Tronche Cedex, France

Abstract

8-(1,1-Dimethylallyl)apigenin has been synthesized in 5 steps from 2’,4’-dibenzylphloroacetophenone and 4-O-methoxyethoxymethylbenzaldehyde. The strategy involved protection of the 4’-hydroxyl in apigenin by a methoxyethoxymethyl group, followed by specific O-prenylation at position 7. Claisen rearrangement of the 7-prenyl-4’-methoxyethoxymethylapigenin performed in one step both the 1,1-dimethylallylation at position 8, and removal of the 4’-methoxyetoxymethyl protecting group.