1. Synthetic Studies of the Flavone Derivatives. VII. The Synthesis of Jaceidin
- Author
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Mitsuru Nakayama, Kenji Fukui, Shigehiro Nakamura, Tokunaru Horie, and Takashi Matsumoto
- Subjects
chemistry.chemical_classification ,chemistry.chemical_compound ,Jaceidin ,chemistry ,Flavone derivatives ,Organic chemistry ,Ether ,Hoesch reaction ,General Chemistry ,Flavones ,Acetophenone ,Catalysis - Abstract
The Hoesch reaction of iretol with methoxyacetonitrile yielded 2,4,6-trihydroxy-3,ω-dimethoxyacetophenone. According to the Allan-Robinson flavone synthesis with O-benzylvanillic anhydride, the acetophenone afforded 4′-benzyloxy-5,7-dihydroxy-3,3′,6-trimethoxyflavone. The catalytic debenzylation of the flavone gave jaceidin, 4′,5,7-trihydroxy-3,3′,6-trimethoxyflavone, which had previously been isolated from Centaurea species. Its triethyl ether was prepared from 3,5-diethoxy-4-methoxyphenol via the corresponding acetophenone, followed by the abovementioned flavone synthesis with O-ethylvanillic anhydride. The ultraviolet spectra of these flavones will also be reported.
- Published
- 1968
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