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
1984 年 33 巻 9 号 p. 628-630
詳細
1984 年 33 巻 9 号 p. 628-630
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.
The reaction of (1) with cis-3-hexenylmagnesium bromide gave 1, 1-dimethoxy-cis-7-decen-4-one (4) in 54% yield. Deacetalization of (4) followed by cyclization afforded 2-(cis-2-pentenyl)-2-cyclopenten-1-one (6) in 48.6% yield. Methyl jasmonate (7) was obtained from (6) in 65% yield.
γ-Jasmolactone (8) was synthesized by an one-pot reaction of methyl 4-oxobutyrate (3) with cis-3-hexenylmagnesium bromide in 69% yield.
