13C NMR-based empirical rules to determine the configuration of fatty acid butanolides. Novel ç-dilactones from Pterogorgia spp
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Diastereomeric ç-dilactones isolated from Pterogorgia spp allowed the establishment of 13C NMR-based empirical rules to determine the relative stereochemistry of 3-alkyl-4-hydroxy-5-methyl-2(5 H)-dihydrofuranones, ç-lactone moieties ubiquitous in many bioactive synthetic and natural products. An NMR-based method using Pirkle's reagent at low temperature allowed the absolute configuration of the naturally occurring dibutenolides to be unambiguously determined. A biogenetic pathway that involves oxidation of long-chain (C16:0 and C18:0) fatty acids is proposed.
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Lorenzo, Manuel, Brito, Inmaculada, Cueto, Mercedes, D'Croz, Luis, and Darias, Jose. 2006. "<a href="https://repository.si.edu/handle/10088/18716">13C NMR-based empirical rules to determine the configuration of fatty acid butanolides. Novel ç-dilactones from Pterogorgia spp</a>." <em>Organic letters</em>, 8, (22) 5001–5004. <a href="https://doi.org/10.1021/ol061572c">https://doi.org/10.1021/ol061572c</a>.