Synthetic studies of rifamycins. III. The partial synthesis of rifamycin ansa-chain compounds from their degradation products.
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概要
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The ansa-chain compound methyl [methyl 2,4,6,8,10,11,12,13,14-nonadeoxy-4,6,8,10,14-penta-<I>C</I>-methyl-3-<I>O</I>-methyl-L-<I>manno</I>-β-D-<I>galacto</I>-(11<I>E</I>,13<I>Z</I>)-11,13-pentadecadienopyranosid]uronate (<B>1a</B>) and its (<I>R</I>)-2-bromo derivative, <B>1b</B>, were transformed into the corresponding 7,9-diacetate <B>3a</B> and <B>3b</B> or the 7,9-acetonide <B>7a</B> and <B>7b</B>. The ozonolysis of <B>3a</B> or <B>3b</B> gave methyl 7,9-di-<I>O</I>-acetyl-2,4,6,8,10-pentadeoxy-4,6,8,10-tetra-<I>C</I>-methyl-3-<I>O</I>-methyl-L-<I>manno</I>-β-D-<I>galacto</I>-undecodialdopyranoside-(1,5) (<B>4a</B>) or its (<I>R</I>)-2-bromo derivative (<B>4b</B>) respectively. The Wittig condensation of <B>4b</B> with (methoxycarbonylmethylene)triphenylphosphorane, followed by debromination with tributylstannane, afforded methyl [methyl-7,9-di-<I>O</I>-acetyl-2,4,6,8,10,11,12-heptadeoxy-4,6,8,10-tetra-<I>C</I>-methyl-3-<I>O</I>-methyl-L-<I>manno</I>-β-D-<I>galacto</I>-(<I>E</I>)-11-tridecenopyranosid]uronate (<B>6a</B>). The diisobutylaluminium hydride reduction of <B>6a</B>, followed by acetonation, gave methyl 2,4,6,8,10,11,12-heptadeoxy-7,9-<I>O</I>-isopropylidene-4,6,8,10-tetra-<I>C</I>-methyl-3-<I>O</I>-methyl-L-<I>manno</I>-β-D-<I>galacto</I>-(<I>E</I>)-11-tridecenopyranoside-(1,5) (<B>10a</B>). The allylic alcohol, <B>10a</B>, was converted into the allylic bromide, <B>12a</B>, which then yielded the triphenylphosphonium bromide, <B>13a</B>. The Wittig condensation of the reactive ylide generated from <B>13a</B> with methyl pyruvate afforded a 4 : 5 mixture of <B>7a</B> and its 13<I>E</I>-isomer. The partial synthesis of <B>1a</B> was accomplished by the selective hydrolysis of the <B>7a</B> isolated from the mixture.
- 公益社団法人 日本化学会の論文
著者
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Nakata Masaya
Department Of Applied Chemistry Faculty Of Science And Technology Keio University
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Sakai Toshiya
Department of Chemical Engineering, Kyushu University
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Tatsuta Kuniaki
Department Of Applied Chemistry Faculty Of Science And Technology Keito University
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Kinoshita Mitsuhiro
Department of Applied Chemistry Engineering Faculty of Keio University
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