Studies on Phenolic Lactones

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  • Part III. Synthesis of (±) Hibalactone

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(±) Hibalactone, α-piperonylidene-β-piperonyl-butyrolactone, was synthesized by the following method. α-Piperonylidene-β-piperonyl-succinic acid dimethylester was reduced with lithium aluminum hydride to 2-piperonylidene-3-piperonyl-1, 4-butanediol, m. p. 117°C. Oxidation of the glycol with manganese dioxide in acetone yielded α-piperonylidene-β-piperonyl-γ-hydroxy-butyraldehyde, which afforded racemic hibalactone, m.p. 154~5°, after oxidation with silver oxide and lactonization.

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