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

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.

SUBMITTER: Ndukwe IE

PROVIDER: S-EPMC7436192 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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

Ndukwe Ikenna E IE Wang Xiao X Lam Nelson Y S NYS Ermanis Kristaps K Alexander Kelsey L KL Bertin Matthew J MJ Martin Gary E GE Muir Garrett G Paterson Ian I Britton Robert R Goodman Jonathan M JM Helfrich Eric J N EJN Piel Jörn J Gerwick William H WH Williamson R Thomas RT

Chemical communications (Cambridge, England) 20200701 55

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, ...[more]

PMID: 32520016

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