A Convenient Synthesis of Methyl Jasmonate and γ-Jasmolactone:Use of 3-Cyanopropionaldehyde Dimethyl Acetal (3-Cyano-1, 1-dimethoxypropane) Derivatives as Precursors of 1, 4-Dicarbonyl Compounds
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概要
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Methyl jasmonate and γ-jasmolactone, as important perfumery constituents, were synthesized from a readily available starting material, 3-cyano-1, 1-dimethoxypropane (1). The synthetic route is shown in Scheme-1.<BR>The reaction of (1) with <I>cis</I>-3-hexenylmagnesium bromide gave 1, 1-dimethoxy-<I>cis</I>-7-decen-4-one (4) in 54% yield. Deacetalization of (4) followed by cyclization afforded 2-(<I>cis</I>-2-pentenyl)-2-cyclopenten-1-one (6) in 48.6% yield. Methyl jasmonate (7) was obtained from (6) in 65% yield.<BR>γ-Jasmolactone (8) was synthesized by an one-pot reaction of methyl 4-oxobutyrate (3) with <I>cis</I>-3-hexenylmagnesium bromide in 69% yield.
- Japan Oil Chemists' Societyの論文
著者
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Saito Shojiro
Department Of Industrial Chemistry Shibaura Institute Of Technology
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MIYAKOSHI Tetsuo
Department of Applied Chemistry, School of Science and Technology, Meiji University
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YOSHIDA Takashi
Nippon Dental University at Niigata
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