59920-27-3

Upstream product

• 115-18-4 2-methyl-3-buten-2-ol 
• 6515-36-2 7-hydroxy-2-phenyl-chroman-4-one 
• 52601-08-8 2',4'-dihydroxy-3',5'-di-C-prenylchalcone 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 6515-05-5 2',4'-bis(methoxymethoxy)acetophenone 
• 249622-68-2 2,4-dimethoxymethoxy3,5-di-C-prenylacetophenone 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Synthesis of 7-hydroxy-6,8-di-C-prenyl-flavanone

The synthesis of flavanone A 8, a constituent of the leaves and bark of Milletia ovalifolia is described. β-Resacetophenone 1 on treatment with methoxymethyl chloride afford 2,4-dimethoxymethoxyacetophenone 2 which on nuclear prenylation yield 2,4-dimethoxymethoxy-3,5-di-C-prenylacetophenone 5. Alkaline condensation of 5 with benzaldehyde give 2',4'-dimethoxymethoxy- 3',5'-di-C-prenylchalcone 6. 2',4'-Dihydroxy-3',5'-di-C-prenylchalcone 7 obtained by the demethoxymethylation of 6, on treatment with NaOAc/EtOH furnish 7-hydroxy-6,8-di-C- prenylflavanone (8, flavanone A).

New Syntheses of Ovaliflavanone-A, Ovaliflavanone-B and Ovalichromene-B

Nuclear prenylation of 7-hydroxyflavanone using 2-methyl-but-3-en-2-ol in the presence of BF3-etherate yields ovaliflavanone-A (II), ovaliflavanone-B (V), 7-hydroxy-6-C-prenylflavanone (IV) and 7-(γ,γ-dimethylallyloxy)-flavanone (III).Nuclear prenylation of 7-hydroxy-3',4'-methylenedioxyflavanone has earlier been shown to yield four products, viz.XI, XII, XIII and XIV.One of them, viz. 7-hydroxy-3',4'-methylenedioxy-8-C-prenylflavanone (XIV) with DDQ furnishes ovalichromene-B (XV).Some of the prenylated compounds from the above flavanones when subjected to DDQ treatment furnish new chromenoflavanones, chromenoflavones and isolonchocarpin.