Issue 5, 2016

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

Abstract

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.

Graphical abstract: Total synthesis of (±)-epithuriferic acid methyl ester via Diels–Alder reaction

Supplementary files

Article information

Article type
Paper
Submitted
17 Nov 2015
Accepted
19 Dec 2015
First published
05 Jan 2016

Org. Biomol. Chem., 2016,14, 1822-1830

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

M. Koprowski, P. Bałczewski, K. Owsianik, E. Różycka-Sokołowska and B. Marciniak, Org. Biomol. Chem., 2016, 14, 1822 DOI: 10.1039/C5OB02368H

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