Yamaguchi-type lactonization as a key step in the synthesis of marine metabolites: (+)-luffalactone.
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.
Basabe
Pilar
P
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caidos 1-5, 37008 Salamanca, Spain. pbb@usal.es
Bodero
Olga
O
Marcos
Isidro S
IS
Díez
David
D
Blanco
Araceli
A
de Román
Mónica
M
Urones
Julio G
JG
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
D006575:Heterocyclic Compounds, 3-Ring; D007783:Lactones; C545689:luffalactone