Journal of the Chemical Society C Organic · 1971 · 14 citations · 0 references
Natural SciencesChemistryMedicinal ChemistryOrganic ChemistryHeterocycle SynthesisHeterocyclic ChemistryMacrocycle SynthesisAromatic Compound BiosynthesisLignan BiosynthesisMedicinal HeterocyclesOxidationSelective Oxidation
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.