Oxidative Coupling of Lignans. II. Non-Phenolic Coupling of Diarylbutane Lignans Related to Matairesinol Dimethyl Ether

The non- phenolic oxidative coupling of some diarylbutane lignans related to matairesinol dimethyl ether (1) has been investigated. Coupling with a thallium(III) oxidant, prepared in situ from thallium(III) oxide and trifluoroacetic acid, converts these lignans efficiently into either dibenzocyclooctadiene or aryltetralin lignans. The dibenzocyclooctadiene lignan (5) prepared from oxidative coupling of matairesinol dimethyl ether has been converted into compound (26) which has significant in vitro antileukaemic activity. The structure of the isostegane (27) formed by oxidative coupling of dimethylbutane (14) has been confirmed by X-ray crystallography.