Access to trans-3,4-Dihydroxy-2-alkylpyrrolidines and Piperidines by Use of Stereodefined Cyclic N,O-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.