Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/25118
Type: Artigo de periódico
Title: The stereochemistry of the Nozaki-Hiyama-Kishi reaction and the construction of 10-membered lactones. The enantioselective total synthesis of (-)-decarestrictine D
Author: Pilli, Ronaldo A.
Victor, Mauricio M.
Abstract: The use of the intramolecular Nozaki-Hiyama-Kishi reaction to construct 10-membered lactones is described. The influence of the nature of the protecting groups at C4 and C5 on the stereochemistry of the newly formed stereogenic center at C7 was investigated. The utility of this methodology has been demonstrated in the stereoselective total synthesis of (-)-decarestrictine D from 1,3-propanediol and polyhydroxybutyrate (PHB) in 13 steps and 6.3% overall yield.
O uso da reação de Nozaki-Hiyama-Kishi para a formação de lactonas de 10 membros é descrita. A influência dos grupos de proteção em C4 e C5 sobre a estereoquímica do novo centro estereogênico formado em C7 foi investigada. A utilidade desta metodologia ficou demonstrada com a síntese total e estereosseletiva da (-)-decarestrictina D a partir do 1,3-propanodiol e poliidroxibutirato (PHB) em 13 etapas e 6,3% de rendimento total.
Subject: decarestrictine D
decanolide
Nozaki-Hiyama-Kishi reaction
lactone
Editor: Sociedade Brasileira de Química
Rights: aberto
Identifier DOI: 10.1590/S0103-50532001000300009
Address: http://dx.doi.org/10.1590/S0103-50532001000300009
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532001000300009
Date Issue: 1-Jun-2001
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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