The total synthesis of (15R)- and (15S)-16-hydroxyferruginol.
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概要
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In order to assign the absolute configuration of C-15 in natural 16-hydroxyferruginol, (5<I>S</I>,10<I>S</I>,15<I>R</I>)- (<B>1a</B>) and (5<I>S</I>,10<I>S</I>,15<I>S</I>)-8,11,13-abietatriene-12,16-diol (<B>1b</B>) have been synthesized. Optical resolution of 2-(2-methoxyphenyl)propanoic acid, prepared from methyl (2-methoxyphenyl)acetate, with cinchonidine afforded (<I>R</I>)- and (<I>S</I>)-enantiomers, which were converted into [(<I>R</I>)-4-methoxy-3-(2-methoxy-1-methylethyl)benzyl]triphenylphosphonium chloride (<B>3a</B>) and its (<I>S</I>)-isomer (<B>3b</B>) respectively. The Wittig reaction of (<I>R</I>)-(−)-α-cyclocitral with <B>3a</B>, followed by partial catalytic hydrogenation and intramolecular cyclization gave (5<I>S</I>,10<I>S</I>, 15<I>S</I>)-12,16-dimethoxy-8,11,13-abietatriene (<B>16a</B>) together with its (5<I>S</I>,10<I>R</I>,15<I>R</I>)-isomer. Similarly, <B>3b</B> was also converted into (5<I>S</I>,10<I>S</I>,15<I>S</I>)-12,16-dimethoxy-8,11,13-abietatriene (<B>16b</B>) and its (5<I>S</I>,10<I>R</I>,15<I>S</I>)-isomer. Demethylation of <B>16a</B> gave <B>1a</B> which was identical with natural 16-hydroxyferruginol. The dimethoxy compound <B>16b</B> was also demethylated to give <B>1b</B>.
- 公益社団法人 日本化学会の論文
著者
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Matsumoto Takashi
Department Of Applied Physics Waseda University
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Imai Sachihiko
Department of Chemistry, Faculty of Science, Hiroshima University
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Miuchi Shigekazu
Department of Chemistry, Faculty of Science, Hiroshima University
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Sugibayashi Hidenori
Department of Chemistry, Faculty of Science, Hiroshima University
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Matsumoto Takashi
Department of Applied Material Science, Faculty of Integrated Arts and Sciences, University of Tokushima
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