大環状ラクトンの合成 1,14-テトラデカノリドの合成

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Erucic acid (I) as starting material has been used to synthesize 1, 14-tetradecanolide in the macrocyclic lactones, which has practical value as musk like odor.<BR>Erucyl bromide (IV) was synthesized by reduction of ethyl erucinonate (II) into erucyl alcohol (III) followed by bromination.<BR>As method (a), prepared the nitrile by usual method, and nitrile was esterified by hydrogen chloride with ethanol, the resulting ethyl ester was reduced to the primary alcohol by lithium aluminium hydride, thus yielding tricosene-14-ol-1 (V). As another method (b), magnesium and formaldehyde were reacted with IV in tetrahydrofurane solution, thus prepared the V.<BR>As next reaction (a), after V was converted to bromide, and this was oxidized with potassium permanganate in acetone solution, obtaining ω-bromomyristic acid (VI). Futhermore, as another reaction (b), V was oxidized with hydrogen peroxide and formic acid, preparing triol, and the resulting triol was treated with lead tetraacetate or periodic acid, thus obtaining ω-hydroxymyristic acid. This was treated with hydrobromic acid to prepare VI.<BR>After VI was converted into the silver salt, cyclized to 1, 14-tetradecanolide (VII) in acetone solution.
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