Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/69076
Type: Artigo de periódico
Title: Hyphenating the Curtius Rearrangement with Morita-Baylis-Hillman Adducts: Synthesis of Biologically Active Acyloins and Vicinal Aminoalcohols
Author: Amarante, GW
Cavallaro, M
Coelho, F
Abstract: Using Morita-Baylis-Hillman adducts as substrates, the Curtius rearrangement was performed in a sequence that allowed the synthesis of several hydroxy-ketones (acyloins) with great structural diversity and in good overall yields. These acyloins in turn were easily transformed into 1,2-anti aminoalcohols through a highly diastereoselective reductive amination step. The synthetic utility of these approaches was exemplified by performing the syntheses of (+/-)-bupropion, a drug used to treat the abstinence syndrome of smoker and (+/-)-spisulosine, a potent anti-tumoral compound originally isolated from a marine source.
Subject: Curtius rearrangement
Morita-Baylis-Hillman
drugs
aminoalcohols
acyloins
Country: Brasil
Editor: Soc Brasileira Quimica
Rights: aberto
Date Issue: 2011
Appears in Collections:Unicamp - Artigos e Outros Documentos

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