Biomimetic total synthesis of (±)-yezo'otogirin A

Org Biomol Chem. 2014 Apr 28;12(16):2519-22. doi: 10.1039/c4ob00186a.

Abstract

The total synthesis of yezo'otogirin A has been achieved via a biosynthetically-inspired strategy. Diastereoselective synthesis of pre-yezo'otogirin A, the proposed biosynthetic pre-cursor of yezo'otogirin A, was accomplished in eight steps from 3-ethoxy-2-cyclohexenone. A biomimetic oxidative radical cyclization was then used to construct the unique tricyclic ring system of yezo'otogirin A. The synthesis showcases the ability of biomimetic radical cyclizations to generate complex natural products from unprotected intermediates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomimetic Materials / chemical synthesis*
  • Biomimetic Materials / chemistry
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Heterocyclic Compounds, 3-Ring