info:eu-repo/semantics/article
First synthesis of (-)-neplanocin C
Fecha
2000-06Registro en:
Comin, Maria Julieta; Rodriguez, Juan Bautista; First synthesis of (-)-neplanocin C; Pergamon-Elsevier Science Ltd; Tetrahedron; 56; 27; 6-2000; 4639-4649
0040-4020
CONICET Digital
CONICET
Autor
Comin, Maria Julieta
Rodriguez, Juan Bautista
Resumen
(-)-Neplanocin C (4), a minor component of the neplanocin family of antibiotics and a lead drug for the design of several conformationally constrained nucleosides analogues, was enantioselectively synthesized starting from D-ribono-1,4-lactone via a convergent approach in twelve steps. The proton NMR spectrum of 4 was in agreement with the corresponding natural product. Calculated coupling constants obtained from ab initio molecular modeling studies and from previously published X-ray structure of neplanocin C also corresponded to the spectroscopic data.