Journal of Chemical and Pharmaceutical Research (ISSN : 0975-7384)

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Original Articles: 2011 Vol: 3 Issue: 4

First Total Synthesis of Three Anti-tyrosinase Activity Prenylated Flavanones from Dalea boliviana

Abstract

The total synthesis of three new prenylated flavanones, (2S)-5,7,2'-trihydroxy-8,3'-diprenylflavanone (I), (2S)-5,2'-dihydroxy-6'',6''-dimethylchromeno-(7,8:2,3'')-3'-prenylflavanone (II) and (2S)-5,7,2'- trihydroxy-5'-(1''',1'''-dimethylallyl)-8-prenyl flavanone (III) was first achieved through C-prenylation, protection of phenolic hydroxyl group, aldolcondensation, cyclization and deprotection starting from substituted benzaldehyde,2,4,6-trihdroxy aceto phenenone and o-hydroxybenzaldehyide,with total yield of 42%. All structures of new compounds were confirmed by IR, 1H NMR and LCMS.