Oxidative degradations of the side chain of unsaturated ent-labdanes. Part II.
A route for the degradation of the side chain of ent-labdane derivatives has been devised, giving the useful synthon 2beta,12-dihydroxy-13,14,15,16,17-pentanor-ent-labdane-8-one (8). The use of this compound in the preparation of terpenylquinone derivatives shall be reported elsewhere. In addition we have synthesized the compound 2beta,12-diacetoxy-8beta,17-epoxy-13,14,15,16-tetranor-ent-labdane (10), which upon catalytic epoxide ring opening in alkaline or acid media gave rise in all cases to the formation of tricyclicc ompounds.
Catalán
Luis Espinoza
LE
Departamento de Química, Universidad Técnica Federico Santa María, Av. España No 1680, Valparaíso, Chile. luis.espinozac@usm.cl
Marín
Karen Catalán
KC
Altamirano
Héctor Carrasco
HC
Fritis
Mauricio Cuellar
MC
Chamy
María Cristina
MC
D004224:Diterpenes / Q000737:chemistry* / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010084:Oxidation-Reduction
D004224:Diterpenes