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

Ikenna E Ndukwe, Xiao Wang, Nelson YS Lam, Kristaps Ermanis, Kelsey L Alexander, Matthew J Bertin, Gary E Martin, Garrett Muir, Ian Paterson, Robert Britton, Jonathan M Goodman, Eric JN Helfrich, Jörn Piel, William H Gerwick, R Thomas Williamson

OAI: oai:www.repository.cam.ac.uk:1810/306637 • DOI: 10.17863/CAM.53723

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.

ANISOTROPY Macrolides Magnetic Resonance Spectroscopy Molecular Conformation Stereoisomerism