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Paper | Regular issue | Vol 38, No. 11, 1994, pp.2463-2472
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6874
An Alternative Route to a Benzofuran Natural Product Dehydrotremetone

Kou Hiroya, Kazuya Hashimura, and Kunio Ogasawara*

*Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-5878, Japan

Abstract

Dehydrotremetone, a toxic ketone isolated from the weeds Eupatorium urticaefolium and Aplopappus heterophyllus, has been synthesized from isovanillin via palladium-mediated cross-coupling reaction and lithium chloride-mediated concurrent demethylation-benzofuran formation reaction. The present procedure also allows a simple preparation of three other non-heterocyclic acetylenic phytotoxic compounds isolated from the culture medium of Eutypa lata.