119680-76-1Relevant academic research and scientific papers
Enantiospecific Syntheses of Aristeromycin and Neplanocin A
Wolfe, Michael S.,Anderson, Blake L.,Borcherding, David R.,Borchardt, Ronald T.
, p. 4712 - 4717 (2007/10/02)
The carbocylic nucleosides (-)-aristeromycin and (-)-neplanocin A were made enantiospecifically in nine steps and ten steps, respectively, from D-ribonic acid γ-lactone.Quenching of an organocuprate conjugate addition reaction with either acetic acid or methanesulfinyl chloride determines whether the divergent synthetic route branches toward (-)-aristeromycin or (-)-neplanocin A.An alternate synthesis of cyclopentenone 1, a common intermediate to these compounds, from D-gulonic acid γ-lactone is also described.
