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http://dx.doi.org/10.5012/bkcs.2014.35.12.3618

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)
Publication Information
Bulletin of the Korean Chemical Society / v.35, no.12, 2014 , pp. 3618-3622 More about this Journal
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%.
Keywords
${\alpha}$-Aminophosphonate; Kebachnik-Fields reaction; Horner-Emmons type condensation; Suzuki coupling; Eupomatenoid-6;
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