Abstract
Pinostrobin (5-hydroxy-7-methoxyflavanone) obtained in relatively large amounts from fingerroot ( Boesenbergia pandurata) was converted to its C-6 and C-8 prenylated derivatives. The Mitsunobu reaction, europium(III)-catalyzed Claisen–Cope rearrangement, and Claisen reaction coupled with cross-metathesis were used as the key steps. Using a sealed-vessel microwave reactor, the Mitsunobu and Claisen/Cope reactions occurred smoothly with short reaction times and in satisfactory yields. The target compounds and five new intermediary substances showed cytotoxic activity toward SK-BR-3, MCF-7, PC-3, and Colo-320DM human tumor cell lines, and all of them had significantly lower IC 50 (μM) values than pinostrobin.
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