Synthesis of 3.BETA.-hydroxytaxodione and coleons S and T.

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概要

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• Hinokiol diacetate was converted into 3β-acetoxyabieta-8,11,13-triene-6β,12-diol <I>via</I> 3β,12-diacetoxyabieta-8,11,13-trien-7-one and 3β,12-diacetoxyabieta-6,8,11,13-tetraene. Oxidation of the 6β,12-diol with benzoyl peroxide produced 3β-acetoxy-12-benzoyloxyabieta-8,11,13-triene-6β,11-diol, which was converted into 3β,11,12-triacetoxyabieta-8,11,13-trien-6-one by lithium aluminium hydride reduction, acetylation, and Jones oxidation. Acidic hydrolysis of the triacetoxy ketone, followed by column chromatography on silica gel, afforded 3β-hydroxytaxodione. Oxidation of the 6β,11-diol with <I>m</I>-chloroperbenzoic acid afforded 3β-acetoxy-12-benzoyloxy-6β-hydroxyabieta-8,12-diene-11,14-dione. This was further converted into 3β,11,14-triacetoxy-12-benzoyloxyabieta-8,11,13-triene-6,7-dione by a series of reactions: Jones oxidation, reduction with zinc powder and dilute hydrochloric acid, acetylation, and Jones oxidation. Alkaline hydrolysis of the 6,7-dioxo compound afforded coleon T, which was isomerized to coleon S by refluxing with concentrated hydrochloric acid in methanol.

• 公益社団法人 日本化学会の論文

著者

• Matsumoto Takashi

  Department of Applied Material Science, Faculty of Integrated Arts and Sciences, University of Tokushima

• Kawashima Hiroyuki

  Department of Chemistry, Faculty of Science, Hiroshima University

• Iyo Koji

  Department of Chemistry, Faculty of Science, Hiroshima University

• Matsumoto Takashi

  Department of Applied Material Science, Faculty of Integrated Arts and Science, University of Tokushima

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