<span style="font-size:12.0pt;font-family: "Times New Roman";mso-fareast-font-family:"Times New Roman";mso-ansi-language: EN-IN;mso-fareast-language:EN-IN;mso-bidi-language:AR-SA" lang="EN-IN">Synthesis of 7-hydroxy-6,8-di-<i style="mso-bidi-font-style:normal">C</i>-prenylflavanone</span>

Abstract

593-595The 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-dimethoxymcthoxyacctophenone 2 which on nuclear prenylation yield 2,4- dimethoxymcthoxy-3 ,5-di-C-prenylacetophenone 5. Alkaline condensation of 5 with benzaldehyde give 2',4'-dimethoxymethox y-3',5' -di-<i style="mso-bidi-font-style: normal">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-<i style="mso-bidi-font-style: normal">C-prenylflavanone (8, flavanone A).<span style="font-family:Symbol;mso-ascii-font-family: " times="" new="" roman";mso-fareast-font-family:hiddenhorzocr;mso-hansi-font-family:="" "times="" roman";mso-char-type:symbol;mso-symbol-font-family:symbol"="" lang="EN-IN"></span