Acidic Rearrangement of (Benzyloxy)chalcones:
A Short Synthesis of Chamanetin

Gabriel Sagrera; Gustavo Seoane

doi:10.1055/s-0029-1217064

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Synthesis 2009(24): 4190-4202
DOI: 10.1055/s-0029-1217064

PAPER

Acidic Rearrangement of (Benzyloxy)chalcones: A Short Synthesis of Chamanetin

Gabriel Sagrera^a, Gustavo Seoane*^b
^a Departamento de Química Orgánica, Facultad de Ciencias, Universidad de la República, C.C. 1157, 11800 Montevideo, Uruguay
^b Departamento de Química Orgánica, Facultad de Química, Universidad de la República, C.C. 1157, 11800 Montevideo, Uruguay
Fax: +598(2)9241906; e-Mail: gseoane@fq.edu.uy;

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Publication History

Received 15 June 2009
Publication Date:
22 October 2009 (online)

Abstract
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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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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.