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13C NMR-based empirical rules to determine the configuration of fatty acid butanolides. Novel γ-dilactones from Pterogorgia spp

AuthorsLorenzo, Manuel; Brito, Inmaculada ; Cueto, Mercedes ; D'Croz, Luis; Darias, José
Issue Date6-Oct-2006
PublisherAmerican Chemical Society
CitationOrganic Letters 8(22): 5001-5004 (2006)
AbstractDiastereomeric γ-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(5H)-dihydrofuranones, γ-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.
Description4 pages, 3 tables, 1 scheme.-- PMID: 17048828 [PubMed].-- Printed version published Oct 26, 2006.
Supporting information available: 1H and 13C NMR spectra of 1-5, 1H NMR of the homoancepsenolide (7) complex with R- and S-TFAE, and experimental procedures.-- Available at: http://pubs.acs.org/doi/suppl/10.1021/ol061572c
Publisher version (URL)http://dx.doi.org/10.1021/ol061572c
Appears in Collections:(IPNA) Artículos
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