76451-13-3Relevant academic research and scientific papers
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.
