title: Yamaguchi-type lactonization as a key step in the synthesis of marine metabolites: (+)-luffalactone.
abstract: A Yamaguchi-type cyclization of 5 and subsequent photochemical oxidation of the furanic ring are the key steps in the first synthesis of the marine metabolite (+)-luffalactone 4 and its epimer at C-16, 16-epi-luffalactone, 27. With this work, we have successfully established the absolute configuration of the natural product. The key intermediate 5 was obtained from the easily accessible diacetate 6a/6b.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caidos 1-5, 37008 Salamanca, Spain. pbb@usal.es
authors.forename: Pilar
authors.initials: P
authors.lastname: Basabe
authors.forename: Olga
authors.initials: O
authors.lastname: Bodero
authors.forename: Isidro S
authors.initials: IS
authors.lastname: Marcos
authors.forename: David
authors.initials: D
authors.lastname: Díez
authors.forename: Araceli
authors.initials: A
authors.lastname: Blanco
authors.forename: Mónica
authors.initials: M
authors.lastname: de Román
authors.forename: Julio G
authors.initials: JG
authors.lastname: Urones
mesh_terms: D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010777:Photochemistry
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D007783:Lactones; C545689:luffalactone