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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 35, Number 12
BKCSDE 35(12)
December 20, 2014 

Expeditious Synthesis of Natural Benzofuran, Eupomatenoid-6 by Umpolung of α-Aminophosphonates
Kongara Damodar, Jong-Gab Jun*
α-Aminophosphonate, Kebachnik-Fields reaction, Horner-Emmons type condensation, Suzuki coupling, Eupomatenoid-6
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, α-aminophosphonate was efficiently employed in this reaction. α-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%.
3618 - 3622
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