The total synthesis of (+)-totarol and (+)-podototarin.
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概要
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The Grignard reaction of 7-methoxyphthalide with methylmagnesium iodide, followed by acetylation and dehydration, gave 3-acetoxymethyl-2-isopropenylanisole which, on catalytic hydrogenation, afforded 3-acetoxymethyl-2-isopropylanisole. This was then converted into (2-isopropyl-3-methoxybenzyl)triphenylphosphonium chloride (<B>8</B>) <I>via</I> 3-hydroxymethyl-2-isopropylanisole and 3-chloromethyl-2-isopropylanisole. The Wittig reaction of (<I>R</I>)-(−)-α-cyclocitral with <B>8</B> in the presence of butyllithium afforded the corresponding styryl derivative, which was converted into the dihydro compound (<B>19</B>) by partial catalytic hydrogenation. The intramolecular cyclization of <B>19</B> gave (+)-totaryl methyl ether (<B>20</B>) along with its <I>cis</I>-isomer. The methyl ether <B>20</B> was finally demethylated with boron tribromide to give (+)-totarol (<B>1</B>), which was further characterized as its acetate. Since the conversion of (+)-<B>1</B> into (+)-podototarin has already been reported, the present work can be regarded as the total synthesis of natural (+)-podototarin.
- 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 Material Science, Faculty of Integrated Arts and Sciences, University of Tokushima
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Suetsugu Akira
Department of Chemistry, Faculty of Science, Hiroshima University
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