Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/202500
Type: Artigo de periódico
Title: The syntheses of the marine metabolites 3-bromoverongiaquinol and 5-monobromocavernicolin
Author: Godoy, Luiz Antonio Fonseca de
Pilli, Ronaldo Aloise
Abstract: An efficient synthesis of the marine metabolite 3-bromoverongiaquinol (1) and the first total synthesis of 5-monobromocavernicolin (2), both isolated from the marine sponge Aplysina cavernicola, have been described based on the 1,2 addition of the lithium enolate of N,O-bistrimethylsilylacetamide (BSA, 4) to 1,4-benzoquinone (3). Bromination and purification of the crude product on silica gel chromatography provided 3-bromoverongiaquinol (1) in 50% overall yield. Under alkaline conditions, the crude product of the bromination reaction was converted to 5-monobromocavernicolin (2) in 20% yield which was also obtained in 13% yield (25% yield based on recovered starting material) from 3-bromoverongiaquinol (1).
Subject: Aplysina cavernicola
3-bromoverongiaquinol and 5-monobromocavernicolin
synthesis
Editor: Sociedade Brasileira de Química
Rights: aberto
Identifier DOI: 10.1590/S0100-40422010001000007
Address: http://dx.doi.org/10.1590/S0100-40422010001000007
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422010001000007
Date Issue: 1-Jan-2010
Appears in Collections:Unicamp - Artigos e Outros Documentos

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