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Type: Artigo de periódico
Title: Synthesis of a bicyclo[6.3.0]undecene skeleton characteristic of some cyclooctanoids by an intramolecular reductive coupling of carbonyls promoted by low-valent titanium
Author: Lima, ELD
Correia, CRD
Abstract: The synthesis of a bicycle[6.3.O]undecene skeleton characteristic of a number of cyclooctanoid natural products is described. The methodology applied relies on an intramolecular reductive coupling of a dialdehyde promoted by low valent titanium to construct the key eight-membered ring. The use of C8K-TiCl3 as an alternative process to the classical coupling developed by McMurry is presented. The dialdehyde 15, precursor of the bicyclo[6.3.0]undecene system, was constructed in a concise manner from 2-carbomethoxy-cyclopentanone in 5 steps with an overall yield of 40%. The key carbonyl coupling of dialdehyde 15 to produce the eight-membered ring proceeded in low yields (similar to 10%) despite several attempts to increase its efficiency.
Subject: cyclooctanoids
carbonyl coupling
low-valent titanium
Country: Brasil
Editor: Soc Brasileira Quimica
Rights: aberto
Date Issue: 1997
Appears in Collections:Unicamp - Artigos e Outros Documentos

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