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

Org Biomol Chem. 2016 Feb 7;14(5):1822-30. 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzofurans / chemistry*
  • Carbazoles / chemical synthesis*
  • Carbazoles / chemistry
  • Cycloaddition Reaction*
  • Molecular Structure
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry
  • Stereoisomerism

Substances

  • Benzofurans
  • Carbazoles
  • Naphthalenes
  • epithuriferic acid methyl ester