76792-94-4Relevant articles and documents
Stereoselective synthesis of flavonoids. Part 4. Trans- and cis-dihydroflavonols
Van Rensburg, Hendrik,Van Heerden, Pieter S.,Bezuidenhoudt, Barend C.B.,Ferreira, Daneel
, p. 14141 - 14152 (2007/10/03)
Epoxidation of a series of poly-oxygenated chalcones with H2O2 in the presence of poly-α-aminoacids yielded chiral aromatic oxygenated oxiranes in moderate to high optical yields. Lewis acid-catalysed phenylmethanethiol ringopening o
Heterocycles. XXII. Stereoselective Synthesis of (+)-Aromadendrin Trimethyl Ether and Its Enantiomer, and Their Reduction
Takahashi, Hiroshi,Li, Shaoshun,Harigaya, Yoshihiro,Onda, Masayuki
, p. 1877 - 1881 (2007/10/02)
Two enantiomeric chalcone epoxides 2a and 2b are synthesized under phase-transfer conditions using 1-benzylquinidinium chloride and 1-benzylquininium chloride as catalysts, respectively.Stereoselective cyclisation of 2a and 2b, followed by methylation and
Some Novel Photochemical and Related Aryl Couplings and Migrations in Flavonoid Synthesis
Westhuizen, Jan H. van der,Ferreira, Daneel,Roux, David G.
, p. 2856 - 2865 (2007/10/02)
2'-Methoxymethoxy-4,4',6'-trimethoxychalcone epoxide couples at the β-position with 3,5-dimethoxyphenol under photolytic conditions to form isomeric 1,3,3-triaryl-2-hydroxypropiophenones.These propiophenones are subject to photo-induced α-ketol rearrangements yielding isomeric 1-hydroxypropan-2-ones.Together these serve as useful synthetic intermediates for 4-arylflavan-3-ones and novel 2-hydroxy-2-arylbenzylbenzofuran-3(2H)-ones and 4-aryl-3-hydroxy-3,4-cis-dihydrocoumarins.The same epoxide reacts ionically under ambient conditions with 2,4,6-trihydroxybenzoic acid to afford a 3-O-benzoylpropiophenone intermediate, which provides novel access to isoflavones in high overall yield.Analogous coupling of phloroglucinol to epoxycinnamates gives diastereoisomeric 3,3-diaryl-2-hydroxypropionates which serve as precursors for 3,4-trans- and 3,4-cis-4-aryl-3-hydroxydihydrocoumarins and thence for 3-aryl- and 3-hydroxycoumarins.