CHEMISTRY OF Saururus cernuus IV: CYCLOOCTADIENE SYSTEMS DERIVED FROM AUSTROBAILIGNAN-5

Article abstract of DOI:10.1016/S0040-4020(01)90001-8

Austrobailignan-5, a 1,4-diarylbutane type neolignan from Sauruus cernuus was converted to a dibenzocyclooctadiene derivative by using two new reagents.The compound was further functionalized by the use of DDQ to mono- and dialcohols.Acid treatment of the monoalcohols led to oxidative demethylenation.The diols were converted to an epoxide and other rearranged products.The stereochemistry of the mono- and dialcohols was established based on nmr and cd spectral data.