Expeditious Synthesis of Natural Benzofuran, Eupomatenoid-6 by Umpolung of α-Aminophosphonates 


Vol. 35,  No. 12, pp. 3618-3622, Dec.  2014
10.5012/bkcs.2014.35.12.3618


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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, 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%.

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  Cite this article

[IEEE Style]

K. Damodar and J. Jun, "Expeditious Synthesis of Natural Benzofuran, Eupomatenoid-6 by Umpolung of α-Aminophosphonates," Bulletin of the Korean Chemical Society, vol. 35, no. 12, pp. 3618-3622, 2014. DOI: 10.5012/bkcs.2014.35.12.3618.

[ACM Style]

Kongara Damodar and Jong-Gab Jun. 2014. Expeditious Synthesis of Natural Benzofuran, Eupomatenoid-6 by Umpolung of α-Aminophosphonates. Bulletin of the Korean Chemical Society, 35, 12, (2014), 3618-3622. DOI: 10.5012/bkcs.2014.35.12.3618.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949