3-ブテン-2-オンを用いるイソラバンジュロール関連化合物の合成

概要

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The title compounds were prepared from the dimer of 3-buten-2-one, 3-methylene-2, 6-heptanedione (1). The reaction of (1) with methylmagnesium chloride in THF gave 2, 6-dimethyl-3-methylene-2, 6-heptanediol (2) in 95% yield. When (2) were treated with various acidic catalysts, it was dehydrated to the corresponding terpene compounds. For example, 2, 2, 6, 6-tetramethyl-3-methylene tetrahydropyrane (3) was obtained by dehydration of (2) with <I>p</I>-toluenesulfonic acid. By treating by (2) with acetic anhydride, 1, 1, 5-trimethyl-4-methylene-5-hexenyl acetate (6) as a new terpene compound and 5-acetoxy-2-isopropylidene-5-methylhexyl acetate (7) were obtained. Isolavandulol acetates (9) and (10) were obtained from diacetate (7).
社団法人日本油化学会の論文