Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Expeditious Synthesis of Natural Benzofuran, Eupomatenoid-6 by Umpolung of α-Aminophosphonates

  • Damodar, Kongara (Department of Chemistry and Institute of Natural Medicine, Hallym University) ;
  • Jun, Jong-Gab (Department of Chemistry and Institute of Natural Medicine, Hallym University)
  • Received : 2014.09.05
  • Accepted : 2014.09.25
  • Published : 2014.12.20
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Abstract

Simple and practical synthesis of natural benzofuran derivative eupomatenoid-6 via Horner-Emmons type condensation as the key step is described. The umpolung property of aldehyde derivative, ${\alpha}$-aminophosphonate was efficiently employed in this reaction. ${\alpha}$-Aminophosphonate of anisaldehyde subjected to Horner-Emmons type condensation with 5-bromo-2-methoxybenzaldehyde to yield the deoxybenzoin, which was further methylated and then underwent tandem demethylation-cyclodehydration to afford the benzofuran scaffold in excellent yield. Finally Suzuki coupling with propenyl boronic acid afforded eupomatenoid-6 with an overall yield of 56.8%.

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References

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