First synthesis of (-)-neplanocin C

(-)-Neplanocin C (4), a minor component of the neplanocin family of antibio tics 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 NM R spectrum of 4 was in agreement with the corresponding natural product. Ca lculated coupling constants obtained from ab initio molecular modeling stud ies and from previously published X-ray structure of neplanocin C also corr esponded to the spectroscopic data. (C) 2000 Elsevier Science Ltd. All righ ts reserved.