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Título

The oxidation profile at C-18 of furanocembranolides may provide a taxonomical marker for several genera of octocorals

AutorDorta, Enrique ; Díaz-Marrero, Ana R. ; Brito, Inmaculada ; Cueto, Mercedes ; D'Croz, Luis; Darias, José
Fecha de publicación4-jul-2007
EditorElsevier
CitaciónTetrahedron 63(37): 9057-9062 (2007)
ResumenThe furanocembranolides 1–3 along with the known compounds pukalide, pukalidealdehyde, epoxypukalide, and leptolide were isolated from Leptogorgia spp. and their structures were determined by spectroscopic evidences. An NMR-based method using Pirkle's reagent at low temperature allowed us to determine the absolute configuration at C-10 of a γ-butenolide unit embedded in a flexible furanocembranolide network. The C-18 of furanocembranolides undergoes an oxidation cascade leading from a methyl group to a carboxylic acid/ester that appears to be genus specific. We introduce the concept genus-specific oxidation, a feature that provides a chemotaxonomical marker for several genera of octocorals. This concept also allowed us to propose a biogenetic pathway for these compounds.
Descripción6 pages, 5 tables, 2 schemes.-- Printed version published Sep 10, 2007.-- Supporting information (19 pages) available at: http://dx.doi.org/10.1016/j.tet.2007.06.080
Versión del editorhttp://dx.doi.org/10.1016/j.tet.2007.06.080
URIhttp://hdl.handle.net/10261/12791
DOI10.1016/j.tet.2007.06.080
ISSN0040-4020
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