INVESTIGADORES
LABADIE Guillermo Roberto
artículos
Título:
Synthesis of the tetracyclic bis-acetal lactone portion of Saudin
Autor/es:
GUILLERMO ROBERTO LABADIE; LILIANA E. LUNA; GONZALEZ SIERRA, MANUEL; CRAVERO, RAQUEL MARIA
Revista:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Editorial:
Wiley
Referencias:
Año: 2003 p. 3429 - 3434
ISSN:
1434-193X
Resumen:
Two synthetic approaches towards the synthesis of the tetracycliclactone 4, containing the caged bis(acetalic) backboneof Saudin, were explored. Both sequences included the utilizationof the known epoxy-acetal 3, prepared stereoselectivelyby means of an intramolecular radical cyclization, asthe common key intermediate, allowing total control over therelative stereochemistry of four consecutive chiral centers.Oxidative degradation with ruthenium dioxide and unsymmetricalozonolysis reactions provided the new two key synthonsin each synthetic route.