スギ(Cryptomeria japonica)材のテルペノイドの単離およびフェルギノールの化学変換

概要

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Resin components of Sugi wood were isolated by silica gel column chromatography from thetoluene-hexane-soluble fraction of the methanol extract of the heartwood. On the other hand, after the heartwood has been directly extracted with hexane, the resin components were separated from the hexane extract. The isolated yields of β-sitosterol, sanndapacopimarlnal, sandaracopimarinol, and ferruginol from the hexane extract were nearly comparable to those from the toluene-hexane-solublefraction of the methanol extract. Ferruginol. isolated from Sugi wood was benzoylated followed by oxidation with Cr03 in acetic acid to give 12-0-benzoylsugiol, from which sugiol was obtained by methanolysis with anionic ion-exchange resin Amberlite IRA-400 in methanol. The oxidation offerruginol with 1.7 equiv. of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in methanol affordedsugiol directly. The reaction of sugiol with 3.3 equiv. of DDQ followed by acetylation gave 12-0-acetyl-5,6-dehyqrosugiol, from which 5,6-dehydrosugiol was synthesized. 6,7-Dehydroferruginol was synthesized from 12-0-benzoylsugiol in 60% yield at 3 steps.
宮崎大学の論文