Access to <i>trans</i>‐3,4‐Dihydroxy‐2‐alkylpyrrolidines and Piperidines by Use of Stereodefined Cyclic <i>N</i>,<i>O</i>‐Acetals as a Diversity‐Generating Element

Abstract

A highly efficient and stereoselective synthetic pathway towards trans-3,4-dihydroxy-2-alkylpyrrolidines and piperidines is described. The nature of the protecting groups on the hydroxyl moieties played a crucial role on the trans selectivity. By using this method, a concise total synthesis of (-)-2-epilentiginosine has been achieved.