An enantiospecific synthesis of the C-21-C-37 segment of the aglycon of amphotericin B.
スポンサーリンク
概要
- 論文の詳細を見る
3-Deoxy-1,2-<I>O</I>-isopropylidene-3-<I>C</I>-methyl-α-D-allofuranose was stereoselectively converted into 3,5-dideoxy-4-<I>O</I>-(methoxymethyl)-3,5-di-<I>C</I>-methyl-6-<I>O</I>-pivaloyl-L-talose ethylene dithioacetal (<B>31</B>) via 3,5-dideoxy-4-<I>O</I>-(methoxymethyl)-3,5-di-<I>C</I>-methyl-L-talopyranuro-6,2-lactone ethylene dithioacetal (<B>24</B>) in 10 steps (23.6% overall yield). Desulfurization [Raney Ni W-4, 92% yield] of <B>31</B> followed by three-step transformation (91% yield) afforded 2,4,6-trideoxy-5-<I>O</I>-(diethylisopropylsilyl)-3-<I>O</I>-(methoxymethyl)-2,4-di-<I>C</I>-methyl-L-altrose, which was olefinated by using methyl (2<I>E</I>,4<I>E</I>)-6-(dimethoxyphosphinyl)-2,4-hexadienoate twice to give the target compound, all-<I>trans</I>-hexaenal <B>4</B> (12 steps, 38.6% overall yield from <B>31</B>).
- 公益社団法人 日本化学会の論文
著者
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Kinoshita Mitsuhiro
Department of Applied Chemistry Engineering Faculty of Keio University
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Taniguchi Masato
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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Takami Hitoshi
Department of Energy Engineering & Science, Nagoya University
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Tamai Tetsuro
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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Takami Hitoshi
Department of Applied Chemistry, Faculty of Science and Technology, Keio University
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