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Diastereoselective Synthesis of Novel Benzofuran Derivatives by Euparin as a Natural Compound with DMAD in the Presence of Trialkyl Phosphite

Research paper by Parvaneh Dastoorani, Malek Taher Maghsoodlou, Mohammad A. Khalilzadeh, Santiago García‐Granda, Laura Torre‐Fernández, Evan Sarina

Indexed on: 09 Mar '16Published on: 17 Dec '15Published in: Heteroatom Chemistry



Abstract

An efficient, simple, and diastereoselective synthesis of novel benzofuran phosphonato ester derivatives has been achieved via a one‐pot three‐component reaction of euparin as a natural product, trialkyl phosphate, and dimethyl acetylenedicarboxylate (DMAD) in diethyl ether without using any catalyst at room temperature. NMR spectroscopic data and X‐ray crystallography analysis are in agreement with the anti arrangement for the two vicinal protons in the structures, and only one diastereoisomer (2S,3R) or (2R,3S) was obtained for the products. The advantage of our research is that this is the first report for the diastereoselective synthesis of phosphonato ester derivatives from a green natural product. This one‐pot reaction occurs in high yields with easy work‐up under mild conditions. All pure products were obtained by recrystallization from ethanol, and there was no need for column chromatography.