American Chemical Society
jo0c00408_si_001.pdf (2.88 MB)

Total Synthesis of the Plant Growth Promoter Auxofuran Featuring a Gold(I) Catalyzed Furan Formation

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journal contribution
posted on 2020-06-04, 13:44 authored by Sibylle Riedel, Martin E. Maier
A concise synthesis of auxofuran (1) was developed. Starting with a Sonogashira cross-coupling reaction, enynol (10) was prepared. A gold­(I) catalyzed cycloisomerization led to disubstituted furan 12. Via an intramolecular Friedel–Crafts cyclization, a dihydrobenzofuranone was obtained. Functional group manipulations, including benzylic oxidation, led to the target molecule.