- Synthesis of fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside based on site-selective deacetylation and deoxygenation
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Fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside were synthesized from commercially available quercetin and naringin in five steps. The key steps are site-selective deacetylation and subsequent deoxygenation. The target molecules were obtained in 37% and 23% yields from the starting materials, respectively.
- Tsunekawa, Ryuji,Hanaya, Kengo,Higashibayashi, Shuhei,Sugai, Takeshi
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- α-HYDROXYDIHYDROCHALCONES AND RELATED 1,3-DIARYLPROPAN-2-ONES FROM XANTHOCERCIS ZAMBESIACA
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Key Word Index-Xanthocercis zambesiaca; Leguminosae; 7,8-dioxyisoflavonoids; α-hydroxydihydrochalcones; 1,3-diarylpropan-2-ones.Abstract-In addition to some previously described 7,8-dioxy-isoflavonoids and 2-benzylbenzofuran-3(2H)-ones the heartwood of Xanthocercis zambesiaca has been shown to contain 7,8,3'-trihydroxy-4'-methoxyisoflavone.These are accompained by the novel α,3,4,4'-tetrahydroxy-2'-methoxydihydrochalcone and its 3-deoxy analogue, the latter of which presumably served as biogenetic precursor for the unique 1-hydroxy-3-(4-hydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl) propan-2-one and its 1-deoxy analogue.Such possible biosynthetic relationship was demonstrated by the facile in vitro transformations of the appropriate α-hydroxydihydrochalcone into the different 1,3-diarylpropan-2-ones.
- Bezuidenhout, S. Catherine,Bezuidenhoudt, Barend C. B.,Ferreira, Daneel
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p. 2329 - 2334
(2007/10/02)
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