Stereospecific synthesis of the C-9-C-16 segment of carbonolide B, the aglycon of carbomycin B.

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概要

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• Stereospecific synthetic routes to methyl (<I>R</I>)-7-hydroxy-(2<I>E</I>,4<I>E</I>)-octadienoate (<B>9</B>) and its (2<I>E</I>,4<I>Z</I>)-isomer (<B>16</B>), the former which can be a useful chemical precursor to the 16-membered-ring aglycon of carbomycin B (carbonolide B), are discussed. Compound <B>9</B>, corresponding to its C-9–C-16 segment, was synthesized starting with methyl 2-deoxy-α-D-<I>arabion</I>-hexopyranoside (<B>2</B>). The deoxysugar <B>2</B> was converted to the masked 2,4,6-trideoxy-D-<I>threo</I>-hexopyranose (<B>6</B>) <I>via</I> the 4,6-dichloro-2,4,6-trideoxy-α-D-<I>lyxo</I>-hexopyranoside derivative. Treatment of <B>6</B> with <I>p</I>-toluenesulfonyl chloride and triethylamine afforded 3-<I>O</I>-acetyl-1,5-anhydro-2,4,6-trideoxy-D-<I>threo</I>-hex-1-enitol, which by reaction with mercury(II) acetate was converted to (<I>R</I>)-5-hydroxy-(2<I>E</I>)-hexenal (<B>8</B>). Reaction of <B>8</B> with Wittig reagent gave the (2<I>E</I>,4<I>E</I>)-isomer <B>9</B>. Compound <B>16</B> was prepared by the Wittig reaction with the 2,3-unsaturated deoxysugar, 2,3,4,6-tetradeoxy-D-<I>glycero</I>-hex-2-enopyranose, which was derived from methyl 2,3-anhydro-4,6-dideoxy-α-D-<I>lyxo</I>-hexopyranoside by treatment with potassium selenocyanate followed by acid hydrolysis.

• 公益社団法人 日本化学会の論文

著者

• Tatsuta Kuniaki

  Department of Applied Chemistry, Faculty of Engineering, Keio University

関連論文

• Synthetic studies of rifamycins. IV. The synthesis of rifamycin ansa-chain compound using carbohydrate.
• Stereospecific synthesis of the C-9-C-16 segment of carbonolide B, the aglycon of carbomycin B.

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