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Total synthesis of (±)-epithuriferic acid methyl ester via Diels–Alder reaction†
Marek Koprowski,Krzysztof Owsianik,Ewa Różycka-Sokołowska,Bernard Marciniak
Organic & Biomolecular Chemistry Pub Date : 01/05/2016 00:00:00 , DOI:10.1039/C5OB02368H
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
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