Synthetic studies toward 3′-C-puromycin analogs

We devised a synthetic scheme based on a Horner–Wadsworth–Emmons olefination followed by a stereoselective reduction in the attempt to synthesize a puromycin analog that cannot be metabolized to a known nephrotoxic 3′-aminonucleoside. This procedure allowed the synthesis of a fully protected nucleoside precursor of the target molecule. However, the last step proceeded with a surprising outcome, providing a dimethyl amide instead of the expected amino ketone derivative.