Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/25166
Type: Artigo de periódico
Title: Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G
Author: Santos, Leonardo S.
Pilli, Ronaldo A.
Abstract: The addition of 5-methyl-2-triisopropylsilyloxyfuran (5) to N-carbobenzyloxy-2-methoxypiperidine (6a) afforded a mixture of the corresponding erythro and threo isomers 7a and 8a, respectively, in moderate to good yields (42-85%) and diastereoisomeric ratio (7a : 8a) ranging from 1.1:1 _ 6:1 depending on the solvent system and the Lewis acid employed. The threo isomer 8a was eventually converted to (+/-)-homopumiliotoxin 223G (1) which was prepared in 5 steps and 13% overall yield from 6a.
A adição de 5-metil-2-tri-isopropilsililoxifurano (5) a N-carbobenziloxi-2-metoxipiperidina (6a) forneceu uma mixtura dos isômeros eritro e treo 7a and 8a, respectivamente, em rendimentos de moderado a bom (42-85%) e razão diastereoisomérica (7a : 8a) variando entre 1,1:1 _ 6:1, dependendo do sistema de solvente e do ácido de Lewis empregados. O isômero treo 8a foi transformado na (+/-)-homopumiliotoxina 223G (1) que foi obtida a partir de 6a em 5 etapas e 13% de rendimento total.
Subject: homopumiliotoxin 223G
N-acyliminium ions
silyloxyfuran
vinylogous addition
Editor: Sociedade Brasileira de Química
Rights: aberto
Identifier DOI: 10.1590/S0103-50532003000600015
Address: http://dx.doi.org/10.1590/S0103-50532003000600015
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600015
Date Issue: 1-Dec-2003
Appears in Collections:Unicamp - Artigos e Outros Documentos

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