Tetrahedron p. 13087 - 13108 (1999)
Update date:2022-08-03
Topics:
Venkateswarlu, Revuru
Kamakshi, Chaldcherla
Moinnddin, Syed G. A.
Subhash, Pithani V.
Ward, Robert S.
Pelter, Andrew
Hursthouse, Michael B.
Light, Mark E.
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.
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