Synthetic studies on pyridomycin. III. Chiral synthesis of (2R,2S)-(-)-2,3-dihydroxy-3-metylpentanoic acid from sugar derivative.
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The Grignard reaction of 3-<I>O</I>-benzyl-6-deoxy-1,2-<I>O</I>-isopropylidene-α-D-<I>xylo</I>-hexofuranos-5-ulose (<B>5</B>) with ethylmagnesium bromide yielded 3-<I>O</I>-benzyl-6-deoxy-5-<I>C</I>-ethyl-1,2-<I>O</I>-isopropylidene-α-D-glucofuranose (<B>6</B>) as a major product in 91% stereoselectivity. Hydrolysis of <B>6</B> followed by successive periodate oxidation and lithium aluminium hydride reduction gave 2-<I>O</I>-benzyl-5-deoxy-4-<I>C</I>-ethyl-D-arabinitol. Selective benzoylation of <B>9</B> followed by successive 3,4-<I>O</I>-isopropylidenation, debenzoylation, hydrogenolysis, and two-stage oxidation with periodate-hypoiodite afforded (4<I>R</I>,5<I>S</I>)-(+)-5-ethyl-2,2,5-trimethyl-1,3-dioxolane-4-carboxylic acid (<B>15</B>) in 24.6% overall yield from <B>5</B>. Hydrolysis of <B>15</B> gave (2<I>R</I>,3<I>S</I>)-(−)-2,3-dihydroxy-3-methylpentanoic acid. The acetonide <B>15</B> is usefull as a synthon for pyridomycin synthesis.
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