Lewis acid- and Bronsted acid-catalyzed stereoselective rearrangement of epoxides derived from himachalenes: access to new chiral polycyclic structures

The acid-catalyzed rearrangement of two enantiomerically pure epoxides derived from sesquiterpernic himachalenes, which are the main components of the essential oil of the Atlas cedar, has been studied using various Lewis and Bronsted acids. Several new polycyclic compounds have been obtained with d...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2011-01, Vol.22 (1), p.101-108
Main Authors: El Haib, Abderrahim, Benharref, Ahmed, Parrès-Maynadié, Sandra, Manoury, Eric, Urrutigoïty, Martine, Gouygou, Maryse
Format: Article
Language:English
Subjects:
Analytical chemistry
Chemical Sciences
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Summary:The acid-catalyzed rearrangement of two enantiomerically pure epoxides derived from sesquiterpernic himachalenes, which are the main components of the essential oil of the Atlas cedar, has been studied using various Lewis and Bronsted acids. Several new polycyclic compounds have been obtained with different selectivities depending upon the catalysts used and the reaction conditions, and were fully characterized by spectroscopic methods. Mechanisms to explain the formation of the different compounds observed in the reaction mixture have also been proposed.
ISSN:0957-4166
1362-511X
0957-4166
DOI:10.1016/j.tetasy.2010.12.013