Add time:09/01/2019         Source:sciencedirect.com

The biological activity of podophyllotoxin has been expressed in terms of the alkylating potential of its “swinging lactone” functionality. The synthesis and characterization of the two isomeric lactones (X and XI) of 3-hydroxymethyl-4-(3,4-methylenedioxyphenyl)-4-hydroxybutanoic acid, embodying the lowest common denominator of this functionality, are described. The attempted preparation of 4.4-diaryl analogs of these dihydroxyacid lactones revealed a novel oxidation-reduction cycle, relating 3-(4,4′-dimethoxybenzhydrylidene)-4-hydroxybutanoic acid lactone (XX) to 3-(α-hydroxy-4,4′-dimethoxybenzhydryl)-4-hydroxy-2-butenoic acid lactone (XXII).

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