17 Lyoniresinolの構造

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The skeleton of lyoniresinol (1, R=R'=H) was determined as 4-aryltetralin, and the position of the two free phenolic hydroxyl groups were confirmed as the formula (1, R=R'=H). The absolute configuration (2R: 3R: 4S) of lyoniresinol was proved as proposed before by degradation. Lyoniresinol dimethyl ether (1, R=CH_3, R'=H) afforded 2α,3α-dideoxylyoniresinol dimethyl ether (23), m.p. 107.5/111.5-112.5°, [α]^<16,9>_<546>+44.5°(CHCl_3, c 4.825) by reduction with LiAlH_4 after tosylation. The compound (23) was ozonized and the proauct cyclized with acetic anhydride followed by pyrolysis. From the pyrolysate, there was obtained (-)-3,4-dimethylcyclopentanone semicarbazone (24), m.p. 206.9-209°, [α]^<23.2>_<546>-114°(CHCl_3, c 0.11) of which absolute configuration had been determined correlating to that of natural (-)-(S)-2-methylbutanol (29) by B. Carnmalm. (+)-3,4-Dimethylcyclopentanone semicarbazone (27), m.p. 205.5-207.5°, [α]^<22.6>_<546>+81°(CHCl_3, c 0.33) was synthesized for the further comparison from (+)-3,4-dimethyladipic acid (25), m.p. 99.3-100°, [α]^<15.3>_<546>+4.27°(CHCl_3, c 6.43), [α]^<17.3>_<546>+2.98°(H_2O, c 6.165).
天然有機化合物討論会の論文
1966-09-15