Coumarins, including heterocycle-linked and fused coumarins, have been reported to possess diverse biological activities and hence are regarded as privileged scaffolds in drug discovery. Consequently, much effort has devoted to not only acquire diverse natural and non-natural compounds bearing novel coumarin skeletons, but also develop efficient synthetic methods thereof. Goniothaline A and B are unprecedented natural pyridocoumarin derivatives isolated from <i>Goniothalamus australis. </i>We report the first total synthesis of goniothaline A and B. The key feature of the synthesis of goniothaline A is high-yielding silver-catalyzed cycloisomerization to afford the pyridine moiety. In addition, goniothaline B, a natural 8-hydroxyquinoline derivative, is readily synthesized by the regioselective demethylation of the goniothaline A.<i> </i>

First total synthesis of natural pyridocoumarins, goniothaline A and B

2019 Fall National Meeting

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