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Master's Dissertation
DOI
10.11606/D.59.1999.tde-15102002-163623
Document
Author
Full name
Ana Lucia Santos de Matos Araújo
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
Ribeirão Preto, 1998
Supervisor
Committee
Constantino, Mauricio Gomes (President)
Marzorati, Liliana
Romero, Jose Ricardo
Title in Portuguese
Estudos sobre a síntese de microbiotol.
Keywords in Portuguese
cuparanos
microbiotol
sesquiterpeno
síntese orgânica
terpeno
Abstract in Portuguese
Neste trabalho descrevemos vários estudos sintéticos realizados com o objetivo de desenvolver um método para a preparação de Microbiotol (1). A estratégia planejada consistiu em preparar o anel ciclopentano que constitui a metade esquerda da fórmula de (1) acima por contração de anel de isoforona (58), e depois juntar uma cadeia aberta que seria posteriormente ciclizada para formar o segundo anel. A contração do anel da isoforona (58) foi realizada de acordo com as reações a seguir: Os compostos de fórmula geral (85) apresenta considerável congestionamento estérico e resistem fortemente à adição de nucleófilos. Neste trabalho desenvolvemos apenas estudos de adição de derivados de levulinato de metila, este mesmo apresentando problemas de reatividade devido a problemas estéricos, e mostramos que este não é o caminho adequado para adicionar um nucleófilo aos compostos (85).
Title in English
Studies on the synthesis of microbiotol synthese.
Keywords in English
cuparenes
organic synthesis
sesquiterpenes
terpenes
Abstract in English
In this work we describe several synthetic studies realized with the purpose of developing a method for the preparation of Microbiotol (1). Our synthetic strategy consisted of preparing the ciclopentane ring which is the left moiety of structure (1) by a ring contraction , starting from isophorone (58), and then add an open chain which would be cyclized to for second ring. The ring contraction was realised according to the following steps. The compounds of general structure (58) have a considerable steric hindrance and are strongly resistant to the addition of a nucleophile. In this work we used only derivatives of methyl levulinate as nucleophiles ; these substrates are themselves sterically hindered, and we showed that this is not the appropriate method to add a nucleophile to compounds (85).
 
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AnaMestrado.pdf (2.64 Mbytes)
Publishing Date
2002-12-04
 
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