Pyridinedithioesters can be used as efficient heterodienophiles when activated by complexation with BF3, 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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