Syntheses of dihydrolavandulol and its related compounds from carboxylic acids and conjugated dienes

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<jats:title>Abstract</jats:title><jats:p>5‐Methyl‐2‐isopropyl‐4‐hexenoic acid, dihydrolavandulic acid <jats:bold>(III)</jats:bold>, was synthesised in 65% yield from 3‐methylbutanoic acid and isoprene with sodium naphthalenide in the presence of <jats:italic>N,N,N′,N′</jats:italic>‐tetramethylethylenediamine. Reduction <jats:bold>of III</jats:bold> with lithium aluminum hydride gave 5‐methyl‐2‐isopropyl‐4‐hexen‐l‐ol, dihydrolavandulol (<jats:bold>IV</jats:bold>) (85% yield). Oxidation of <jats:bold>IV</jats:bold> with pyridinium chlorochromate gave 5‐methyl‐2‐isopropyl‐4‐hexenal, dihydrolavandulyl aldehyde (<jats:bold>V</jats:bold>) (81 % yield).</jats:p>

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