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L'epoxy-pyronène : Synthon d'accès aux cyclocitrals et aux ionones et précurseur de nouveaux composés terpénoïdes

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
50
Issue
11
Identifiers
DOI: 10.1016/s0040-4020(01)87017-4

Abstract

Abstract The selective obtention of epoxy-pyronene from δ-pyronene has been realized using metachloroperbenzoïc acid. The isomerization of this epoxydic compound with Lewis and protonic acids and on active alumina has been studied leading to cyclocitrals. Ionones are obtained from epoxy-pyronene by homologation with various C 3 units, in the presence of paratoluenesulfonic acid in order to obtain β-cyclocitral in situ. New terpenic compounds with the cyclogeranyl skeleton were obtained from epoxy-pyronene by reduction followed by homologation.

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