A simple and efficient synthesis of optically active (+)-4-demethoxydaunomycinone.
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概要
- 論文の詳細を見る
Diels-Alder reaction of 2-chloro-1,3-butadiene with anthracene-1,4,9,10-tetrone was found to occur exclusively at the external (C<SUB>2,3</SUB>) double bond, giving the adduct in an excellent yield. The adduct was elaborated to 5,12-dihydroxy-1,2,3,4-tetrahydro-2,6,11-naphthacenetrione. The conventional cyanohydrin formation of this sample followed by acid hydrolysis gave (±)-2,5,12-trihydroxy-6,11-dioxo-1,2,3,4-tetrahydro-2-naphthacenecarboxylic acid. The racemic acid was found to be cleanly resolved by forming a salt with (−)-<I>N</I>-methylephedrine, furnishing optically pure (<I>R</I>)-carboxylic acid. Successive treatments of the (<I>R</I>)-carboxylic acid with <I>N</I>,<I>N</I>′-carbonyldiimidazole and methylmagnesium bromide in the presence of trimethylsilyl triflate readily produced optically pure (<I>R</I>)-(−)-7-deoxy-4-demethoxydaunomycinone, the key synthetic intermediate of (+)-4-demethoxydaunomycinone.
- 公益社団法人 日本化学会の論文
著者
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Terashima Shiro
Sagami Chemical Res. Inst.
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SUZUKI MICHIYO
Sagami Chemical Research Center
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MATSUMOTO TERUYO
Sagami Chemical Research Center
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KIMURA YOSHIKAZU
Sagami Chemical Research Center
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Abe Rumiko
Sagami Chemical Research Center
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