Lorenzo Manuel, Brito Inmaculada, Cueto Mercedes, D'Croz Luis, Darias José
Instituto de Productos Naturales y Agrobiología del CSIC, Avenida Astrofísico F. Sanchez 3, 38206 La Laguna, Tenerife, Spain.
Org Lett. 2006 Oct 26;8(22):5001-4. doi: 10.1021/ol061572c.
Diastereomeric gamma-dilactones isolated from Pterogorgia spp allowed the establishment of (13)C NMR-based empirical rules to determine the relative stereochemistry of 3-alkyl-4-hydroxy-5-methyl-2(5H)-dihydrofuranones, gamma-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. [structure: see text]
