Hydnocarpin D was isolated from the flowering plant Hydnocarpus anthelminthic in family Flacourtiaceae, as a racemic mixture devoid of optical activities, in an extremely limited amount. Racemic Hydnocarpin D has been reported to have promising anti-proliferative potency towards a human DU145 prostate cancer cell line. There are no reports, however, on the anti-proliferative potency of its optically pure enantiomers. Also, no other anticancer activity has been reported for hydnocarpin D due to the supply issue. This study aims to synthesize the (10S,11S)- and (10R, 11R)-hydnocrapin D. So far the key intermediate, 4',5,7-O-tri(p-methoxybenzyl)luteolin has been synthesized from naturally abundant hersperidin. The six-step reaction procedure that was employed to synthesize this intermediate includes dehydrogenation, benzylation, glucoside hydrolysis, and selective demethylation, phenol protection and selective debenzylation. Also, another key intermediate containing the phenylpropanoid moiety with R,R and S,S-configuration at C-1 and C-2 has been synthesized through a six-step transformation.

Studies toward total synthesis of enantiopure hydnocarpin D

2019 Spring National Meeting

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