Transformations of lignans, Part V. Reactions of DDQ with a gmelinol hydrogenolysis product and its derivatives

Article abstract of DOI:10.1016/S0040-4020(99)00801-7

Hydrogenolysis of gmelinol 8 with sodium in liquid ammonia gives a triol 9, which is converted under various reaction conditions into a range of derivatives including the di- and tri-O-methyl ethers 10 and 11, a 3,4- dibenzyl-3-hydroxy-tetrahydrofuran 12, and its acetate 13. These derivatives undergo oxidative cyclisation with DDQ in acetic acid or trifluoroacetic acid to yield 1-aryltetralin, 1-arylnaphthalene, dibenzocyclooctadiene and spirodienone derivatives in reactions which provide biomimetic analogies for biogenetic transformations of lignans.