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Type: Artigo de periódico
Title: Studies towards the construction of alkylidene quinolizidines. The total synthesis of homopumiliotoxin 223G
Author: Santos, LS
Pilli, RA
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.
Subject: homopumiliotoxin 223G
N-acyliminium ions
vinylogous addition
Country: Brasil
Editor: Soc Brasileira Quimica
Citation: Journal Of The Brazilian Chemical Society. Soc Brasileira Quimica, v. 14, n. 6, n. 982, n. 993, 2003.
Rights: aberto
Identifier DOI: 10.1590/S0103-50532003000600015
Date Issue: 2003
Appears in Collections:Unicamp - Artigos e Outros Documentos

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