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Synthesis 2009(24): 4190-4202
DOI: 10.1055/s-0029-1217064
DOI: 10.1055/s-0029-1217064
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Acidic Rearrangement of (Benzyloxy)chalcones: A Short Synthesis of Chamanetin
Further Information
Received
15 June 2009
Publication Date:
22 October 2009 (online)
Publication History
Publication Date:
22 October 2009 (online)
Abstract
Treatment of (benzyloxy)chalcones with trifluoroacetic acid in refluxing chloroform gave several new benzyl(hydroxy)flavanones in high yields and good regioselectivities. By using this procedure, we prepared the natural compound chamanetin in good yield from readily available reagents.
Key words
benzylation - rearrangements - protecting groups - chamanetin - chalcones
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References
For compound 59, the atom that contributes more to the formation of the HOMO is C8, in agreement with the preferred position for the attack to the benzyl cation (Figure [³] ); however, the data calculated for 58 indicate an opposite trend.