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| LETTER | Synlett 2006: 1607-1609
DOI: 10.1055/s-2006-941596 |
© Georg Thieme Verlag Stuttgart · New York
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A Convenient Entry to 5-(sp2)-Substituted and 5,5-Disubstituted Tetronic Acids
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| 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;
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Received
2 February 2006 |
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
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