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Synlett 2006(10): 1607-1609  
DOI: 10.1055/s-2006-941596
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Entry to 5-(sp2)-Substituted and 5,5-Disubstituted Tetronic Acids

David Tejedor, Alicia S antos-Expósito, Fernando García-Tellado*
Instituto de Productos Naturales y Agrobiología, CSIC, Avda. Astrofísico Francisco Sánchez 3, 38206 La Laguna, Tenerife, Canary Islands, Spain
Fax: +34(922)260135; e-Mail: fgarcia@ipna.csic.es;
Further Information

Publication History

Received 2 February 2006
Publication Date:
12 June 2006 (online)

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Abstract

A one-pot, convenient and general access to 5-sp2-substituted and 5,5-disubstituted tetronic acids is described. The protocol embodies two consecutive chemical events: a Michael addition of pyrrolidine on a secondary or tertiary γ-hydroxy-α,β-alkynyl ester derivative to give the corresponding enamine, and the subsequent acid-catalyzed hydrolysis-lactonization of this intermediate to afford the tetronic acid derivative.

Key words

alkynes - lactones - aminations - cyclizations - Michael additions

    References and Notes

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1

Associate researcher at the Instituto Canario de Investigación del Cáncer, www.icic.es.