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《Acta Pharmaceutica Sinica》 1985-01
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STUDIES ON SYNTHESIS OF 6, 8-DIMETHYL-5, 7, 4′-TRI HYDROXYL FLAVANONE

LIANG Xiao-Tian, CHEN Shu-Feng, LU Yu-Hua and GE Da-Lun(Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing)  
Farrerol (Ⅴ) has been isolated from the leaves of Rhododendron dauricurn L. (Man-Shan-Hong) of Heilongjiang province. Its structure is ascertained s 6, 8-dimethyl-5,7,4′-trihydroxyflavanone, which is a phlegm-reducing principle.We report here two routes of syntheses for farrerol (Ⅴ). The first is condensation of compound Ⅰ with compound Ⅳ to give compound Ⅵ, followed by a Fries reaction and cyclization. The second route makes use of the condensation of compound (ⅩⅣ) with p-hydroxybenzaldehyde (Ⅻ) in the presence of boric acid using ethylene glycol as a diluent.Synthetic (±)-farrerol was found to be identical with the natural specimen by IR and NMR spectra. They were also comparable pharmacologically, toxicologically and clinically.
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【Co-references】
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