The lignan, helioxanthin (III), has been synthesized from 2-bromo-4,5-methylenedioxyphenylpropiolic acid (VII) by treatment with dicyclohexylcarbodi-imide to give the dibromophenylnaphthalenedicarboxylic acid anhydride (VIII), followed by reductive debromination to the diol (VI) and selective oxidation by silver carbonate–Celite to the lactone (III). Some by-products obtained in the conversion of (VII) to (VIII) are described.
T. L. Holmes and R. Stevenson, J. Chem. Soc. C, 1971, 2091 DOI: 10.1039/J39710002091
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