Syntheses of ( + )-Phrymarolin II and Its Stereoisomers |
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| Authors: | Fumito Ishibashi Eiji Taniguchi |
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| Institution: | Department of Agricultural Chemistry, Faculty of Agriculture, Kyushu University, Hakozaki 6–10–1, Higashi-ku, Fukuoka 812, Japan |
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| Abstract: | Phrymarolin II, a unique naturally-occurring lignan having a 1,2-dioxygenated 3,7-dioxabicyclo3.3.0]octane skeleton, was synthesized by the reaction of sesamol, in the presence of cadmium carbonate, with 1-acetoxy-2-chloro-6-(2′-methoxy-4′,5′-methylenedioxyphenyl)-3,7-dioxabicyclo3.3.0]octane. The latter was prepared through 13 steps starting from an aldol condensation of β-vinyl-γ-butyrolactone with 2-methoxy-4,5-methylenedioxybenzaldehyde. Three diastereomers of phrymarolin II were also obtained. |
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