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Paper | Regular issue | Vol 75, No. 8, 2008, pp.1971-1981
Published online, 8th April, 2008
DOI: 10.3987/COM-08-11370
Halolactonization of γ-Acetylenic Acids: Synthesis of Novel Spiroisoindole Halobutyrolactones

Mohamed M. Rammah, Mohamed Othman,* Moncef Msaddek, and Mohamed B. Rammah

*URCOM, Faculty of Sciences and Techniques, University of Le Havre, 25 Rue Philippe Lebon, BP 540, F-76058 Le Havre Cedex, France

Abstract

Acetylenic carboxylic acids are cyclized to spirohalo butyrolactones, in the presence of NBS or NIS and K2CO3. The corresponding 5(E)-haloalkylidene-spirobutyrolactones were isolated in high yields, and this process constitutes an easy and efficient route to analogous structures of natural products of biological interest.