76 シダ植物成分:ハコネシダ葉の主トリテルペノイド,Adian-5-ene ozonideの構造決定とHopaneおよびMigrated Hopane系mono-ene等のオゾン酸化反応について

概要

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Hexane extraction of the fresh leaves of Adiantum monochlamys collected in October afforded a triterpenoid, m.p.154-157°, [α]_D +19.4°, as a main constituent(0.12%), which has been concluded to be adian-5-ene ozonide(1). 1 was proved to be identical with a sole crystalline product of ozone-oxidation of adian-5-ene(2) in a hexane solution. To compare with the case of adian-5-ene, various mono-enes of hopane and migrated hopane series were subjected to ozone-oxidation. The results obtained were quite interesting because only two of the ten compounds gave the stable ozonides, three gave epoxides and the othersafforded quite complicated mixtures as shown as follows: a. Only stable epoxides were obtained, neohop-18-ene(α- and β-epoxides); pteron-14-ene (β-epoxide) fern-7-ene(α-epoxide) b. Stable ozonides were obtained, hop-17(21)-ene(α and β-ozonide, 1:1); adian-5-ene(α-O-O-) c. Various products including decomposition products of epoxides and/or ozonides were obtained, neohop-13(18)-ene, fern-9(11)-ene, adian-1(10)-ene, filic-3-ene, hop-21-ene etc. Glutin-5-ene (migrated oleanene) gave also a stable ozonide(α-O-O-). There have been reported various reaction mechanisms of ozone-oxidation, among which P.R. Story's proposal seems to be favourable to explain the above results.
天然有機化合物討論会の論文
1978-08-22