The association of gilvocarcin-type C-glycosides with duplex DNA likely underlies the antitumor activity displayed by members of this family of natural products. With the aim of studying the interaction of polycarcin V and its derivatives with duplex DNA, a convergent total synthesis (7.4% yield) of this naturally occurring a-C-aryl glycoside from protected rhamnose, naphthol, and iodoarenecarboxylic acid fragments was developed. The synthetic pathway features a stereoselective C-glycosylation reaction for the union of the carbohydrate and aromatic moieties.

Total synthesis of polycarcin V and exploration of its DNA-binding properties<i>
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248th National Meeting (2014)

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