35492-16-1

Upstream product

• 26207-83-0 (+/-)-3t-hydroxy-2r-(4-hydroxy-phenyl)-5,7-dimethoxy-chroman-4-one 
• 77-78-1 dimethyl sulfate 
• 76436-29-8 2-Hydroxy-4,6-dimethoxy-benzoic acid 2-hydroxy-3-(2-hydroxy-4,6-dimethoxy-phenyl)-1-(4-methoxy-phenyl)-3-oxo-propyl ester 
• 480-20-6 (+/-)-aromadendrin 

Downstream Products

• 1098-92-6 kaempferol 5,7,4'-trimethyl ether 
• 29063-52-3 (2R^*,3S^*,4S^*)-5,7,4'-trimethoxyflavan-3,4-diol 
• 29063-52-3 (2R^*,3S^*,4R^*)-5,7,4'-trimethoxyflavan-3,4-diol 
• 15486-33-6 4',7,-di-O-methylkaempferol 
• 15486-34-7 5-hydroxy-3,4',7-trimethoxyflavone 
• 16692-52-7 3,4',5,7-tetramethoxyflavone 

Relevant academic research and scientific papers

HETEROCYCLES. XVIII. SYNTHESIS OF THE RACEMATES OF NATURALLY OCCURRING FLAVONOIDS

Racemic aromadendrin and fustin have been stereoselectively synthesized.Reduction of the O-substituted derivatives of these flavanonols provides the corresponding derivatives of gleditsin, leucopelargonidin and mollisacacidin (leucofisetinidin).

Some Novel Photochemical and Related Aryl Couplings and Migrations in Flavonoid Synthesis

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.