23 ジテルペンフェノールの合成 : FerruginolおよびTanshinoneの合成

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概要

• 論文の詳細を見る

• Two novel synthetic methods have been developed for the synthesis of phenolic diterpenoids. One of which is a base catallized condensation of a β-dicarbonyl compound with a β-alkoxyvinyl ketone to give a 2-acylphenol, and the another method involves quaternization of a γ-ketoalkylisoxazole, followed by treatment with aqueous base to yield a 2-acylphenol. Application of the latter method made possible a total synthesis of ferruginol from known decalone (20) via an isoxazole derivative(22) as shown in the figure. Tanshinone-II and Cryptotanshinone, diterpenoid pigments of Salvia miltorrhiza, were synthesized by 16 steps from 1,2,4-trimethoxybenzene. The methoxybenzene was converted by usual methods into the trimethoxydecalone(7), which on condensation with γ-bromocrotonic ester followed by palladium catallized isomerization afforded a naphthylbutyric ester (9). Succesive treatments of the ester (9) with methyl Grignard reagent and sulfuric acid gave a hydrophenanthrene(11) which was converted into the acylphenanthrene derivative (15) by the methods shown in the figure. One of the two methoxy groups in compound (15) was selectively hydrolyzed by BCl_3 to give a acylnaphthol (16), which was converted into the naphthofurane (18) by the usual methods. By heating with excess methyl Grignard reagent, methoxy group in the naphthofurane (18) was hydrolyzed and afforded a unstable furanonaphthol (19), which was oxidized with Fremy's salt to give the Tanshinone-II, identical with the natural compound in all respects.

• 天然有機化合物討論会の論文
• 1967-09-25

著者

• 立石 満

  東教大理学部

• 柿沢 寛

  Department of Chemistry, Tokyo Kyoiku University

• 井上 幸信

  筑波大化

• 大橋 守

  東教大理学部

• 丸石 照機

  東教大理学部

• 井上 幸信

  東教大理学部

• 柿沢 寛

  東教大理学部

• 柿沢 寛

  Department Of Chemistry Tokyo Kyoiku University

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