One‐Pot Synthesis of DHA Homologues from Carboxylic Acids and Evaluation of Their Antitumor Cytotoxicity

Abstract It is found that CF 3 SO 3 H/(CF 3 CO) 2 O‐mediated cross‐acylation acetic acid with bulky substituted acetic acids RCH 2 COOH (R = i Pr, t Bu, 1‐adamantyl) proved to be the simple and convenient method for the synthesis of lipophilic dehydroacetic acid homologues. The conditions of deacylation of symmetrical α‐pyrones with subsequent acylation with adamantyl acetic acids have been developed, leading to an expansion of available derivatives of dehydroacetic acid. It has also been shown that adamantylacetone is readily formed by cross‐acylation of malonic acid and adamantyl acetic acid. Enamines derived from obtained α‐pyrones show strong cytotoxic activity against HeLa human cell lines.