Stereoselective synthesis of (-)-trachelanthic acid and (+)-viridifloric acid, necic acid components of pyrrolizidine alkaloids from a common intermediate.
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概要
- 論文の詳細を見る
Diastereoselective reduction of a side-chain keto group in (2<I>S</I>,5<I>R</I>)-5-acetyl-2-(<I>t</I>-butyl)-5-isopropyl-1,3-dioxolan-4-one (<B>5</B>) with (<I>i</I>-Bu)<SUB>2</SUB>AlH in ether afforded (1′<I>S</I>,2<I>S</I>,5<I>R</I>)-2-(<I>t</I>-butyl)-5-(1′-hydroxyethyl)-5-isopropyl-1,3-dioxolan-4-one (<B>6</B>), while reduction of <B>5</B> with LiBH(<I>s</I>-Bu)<SUB>3</SUB> in ether gave the (1′<I>R</I>)-isomer <B>7</B> predominantly. (−)-Trachelanthic acid (<B>1</B>) and (+)-viridifloric acid (<B>2</B>) were synthesized upon hydrolysis of <B>6</B> and <B>7</B>, respectively.
- 公益社団法人 日本化学会の論文
著者
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Niwa Haruki
Department Of Applied Physics And Chemistry The University Of Electro-communications
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Yamada Kiyoyuki
Department Of Chemistry Faculty Of Science Nagoya University
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Ogawa Takeshi
Departmen Of Orthopaedic Surgery Nihon University School Of Medicine
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Ogawa Takeshi
Department of Chemistry, Faculty of Science, Nagoya University
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