Swinholide‐A, a new marine macrolide. Complete assignment of 1H and 13C spectra by 2D NMR techniques

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Abstract

1H and 13C NMR spectra of the novel marine macrolide swinholide‐A, which provide the basis for its structure elucidation, have been completely assigned by parallel use of 1D and homo‐ and hetero‐nuclear 2D NMR techniques. Swinholide‐A (1) probably a polyketide, is a 22‐membered macrolide embodying a dihydropyran ring and a 10‐carbon side‐chain ending with a substituted tetrahydropyran ring. The high degree of overlap of eleven CH—O and nine CH2 signals in the 1D proton NMR spectrum of 1 necessitated the structure elucidation of swinholide‐A tetraformate (2) by 2D homo‐ (up to 6J with formyl groups) and hetero‐nuclear NMR correlations. Formyl groups can be good structural probes in complex polyalcohols, as shown by the observed 5J and 6J formate couplings in 2.

Original languageEnglish
Pages (from-to)343-349
Number of pages7
JournalMagnetic Resonance in Chemistry
Volume24
Issue number4
DOIs
StatePublished - Apr 1986

Keywords

  • 2D NMR
  • long range couplings
  • marine sponge
  • polyketide

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