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A convenient method for the preparation of γ-arylidene-α,β-unsaturated γ-lactones:Application to the synthesis of the thiophene lactone obtained from Chamaemelum nobile L

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
27
Issue
22
Identifiers
DOI: 10.1016/s0040-4020(01)91710-7

Abstract

Abstract A facile synthesis of γ-arylidine-α,β-unsaturated γ-lactones was achieved: a keto lactone (e.g., 4) which is readily obtained from a keto acid ( 1) was dehydrated to conjugated lactones ( 9 and 10) with acetic anhydride in the presence of either p-toluenesulfonic acid or sodium acetate. By application of this unusual dehydration reaction, a natural product, the thiophene lactone ( 13) was synthesized. Some reactions of the conjugated lactone ( 9) were carried out, leading to the formation of unsaturated γ-lactams ( 19 and 20).

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