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

✍ Scribed by Shmuel Carmely; Michal Rotem; Yoel Kashman


Publisher
John Wiley and Sons
Year
1986
Tongue
English
Weight
738 KB
Volume
24
Category
Article
ISSN
0749-1581

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✦ Synopsis


H and =CNMR 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 uf overlap of eleven CH-0 and nine CH, 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 "J and 6J formate couplings in 2.


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