title: 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.
authors.affiliation: Department of Chemistry, POSTECH (Pohang University of Science and Technology), Pohang, 790-784 (Korea).
authors.forename: Soyeong
authors.initials: S
authors.lastname: Kang
authors.forename: Dong-gil
authors.initials: DG
authors.lastname: Kim
authors.forename: Young Ho
authors.initials: YH
authors.lastname: Rhee
keywords: diastereoselectivity; enantioselectivity; heterocycles; natural products; synthetic methods