Pyridinedithioesters as heterodienophiles: application to the synthesis of aprikalim |
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Authors: | Bastin Reyhan Albadri Hashim Gaumont Annie-Claude Gulea Mihaela |
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Affiliation: | Laboratoire de Chimie Moléculaire et Thio-Organique (UMR CNRS 6507), ENSICAEN, Université de Caen, 6, Bd. Maréchal Juin, 14050 Caen, France. |
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Abstract: | [reaction: see text] Pyridinedithioesters can be used as efficient heterodienophiles when activated by complexation with BF(3), by protonation, or by oxidation of the nitrogen atom of the pyridine moiety. The hetero-Diels-Alder reaction using 3-pyridinedithioester as a heterodienophile was the key step in a new synthesis of Aprikalim in racemic form. The methodology can be reliably extended to prepare new analogues of Aprikalim. |
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