Total synthesis of (±)-epithuriferic acid methyl ester via Diels-Alder reaction.

Org Biomol Chem

Jan Długosz University in Częstochowa, Institute of Chemistry, Environmental Protection and Biotechnology, The Faculty of Mathematics and Natural Sciences, Armii Krajowej 13/15, Częstochowa, 42-201, Poland.

Published: February 2016

In this paper, we have described the first total synthesis of (±)-epithuriferic acid methyl ester from non-natural sources, in four steps (20% overall yield). The key step involves the Diels-Alder reaction of isobenzofuran with methyl 3-(dimethoxyphosphoryl)acrylate which is controlled by "ortho" regio- and endo stereoselectivities due to the COOMe group.

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http://dx.doi.org/10.1039/c5ob02368hDOI Listing

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