36 メソ型化合物を用いる光学活性プロスタグランディン,ステロイド中間体の新合成法

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概要

• 論文の詳細を見る

• Aiming to overcome several inefficient aspects of ordinary chemical resolution of racemic compound, we have developed the new methodology which recommends utilization of symmetrically functionalized meso-compound as a resolution substrate in place of racemic compound. As shown in Scheme I, when meso-compound(1) is monofunctionalized by a chiral compound and each of the formed diastereomers (2 and 3), separable by fractional recrystallization or chromatography, is submitted to further chemical elaboration including protective group transposition, it is theoretically possible to convert the total amount of the starting material into one requisite optically pure synthetic intermediate(6 or 7) by selecting synthetic operations. By employing this novel concept, the optically pure prostaglandin intermediate(Scheme II, (-)-9) has been prepared from the meso-diol(8) via the two diastereomers(10 and 11) which are produced by the reaction of 8 and N-methanesulfonyl-(S)-phenylalanyl chloride. In a similar manner, another optically pure prostaglandin intermediate(Scheme III, (-)-19) and optically pure steroid intermediate(Scheme IV, (-)-25) have been successfully synthesized from the corresponding meso-diols(18 and 24), respectively. These successful results seem to clearly disclose wide generality of the exploited novel methodology.

• 天然有機化合物討論会の論文
• 1978-08-22

著者

• 山田 俊一

  東京大学

• 寺島 孜郎

  (財)相模中央化学研究所

• 奈良 宗彦

  興和(株)東研

• 山田 俊一

  城西大・薬

• 寺島 孜郎

  東大・薬

• 寺島 孜郎

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address)sagami Chemical Research Cen

関連論文

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• Studies on Optically Active Amino Acids. XIV. Studies on α-Alkyl-α-amino acids. VII. Determination of Absolute Configuration of Optically Active α-Methylphenylglycine Configuration of Optically Active α-Methylphenylglycine and 1-Methyl-1-phenylpropylamine
• 日本薬学会学術賞受賞 古賀憲司氏の業績
• 名誉会員管澤重彦先生を偲びて
• オクテット
• オクテット
• 光学活性化合物に魅せられた50年 : 山田俊一先生にきく
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