Synergism of anisotropic and computational NMR methods reveals the likely configuration of phormidolide A

Chem Commun (Camb). 2020 Jul 9;56(55):7565-7568. doi: 10.1039/d0cc03055d.

Abstract

Characterization of the complex molecular scaffold of the marine polyketide natural product phormidolide A represents a challenge that has persisted for nearly two decades. In light of discordant results arising from recent synthetic and biosynthetic reports, a rigorous study of the configuration of phormidolide A was necessary. This report outlines a synergistic effort employing computational and anisotropic NMR investigation, that provided orthogonal confirmation of the reassigned side chain, as well as supporting a further correction of the C7 stereocenter.

MeSH terms

  • Anisotropy
  • Macrolides / chemistry*
  • Magnetic Resonance Spectroscopy / methods*
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Macrolides
  • phormidolide