Base-catalyzed isomerization of retinoic acid. Synthesis and differentiation-inducing activities of 14-alkylated all-trans-, 13-cis-, and 20, 14-retro-retinoic acids

…, H Kagechika, E Kawachi, H Fukasawa…

Index: Tanaka; Kagechika; Kawachi; Fukasawa; Hashimoto; Shudo Journal of Medicinal Chemistry, 1992 , vol. 35, # 3 p. 567 - 572

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Citation Number: 9

Abstract

Retinoic acid (1) is isomerized regioselectively by excess amounts of lithium diisopropylamide (LDA) to give 20, 14-retro-retinoic acid (3). Alkylation of the intermediate dianion of retinoic acid gave 14-alkylated derivatives of 3. By isomerization of the alkylated retro isomers under basic conditions, several 14-alkyl-all-trans-and-13-cis-retinoic acids were synthesized. The retinoidal activities of these derivatives were examined, based on ...