Asymmetric routes toward polyhydroxylated pyrrolidines: Synthesis of 1,4-dideoxy-1,4-imino-d-galactitol and 1,4-dideoxy-1,4-imino-d-glucitol.

Giuliana Righi, Emanuela Mandic', Carla Sappino, Ergys Dema, Paolo Bovicelli

Carbohydrate research 2016 Nov 29

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Herein the total synthesis of the pyrrolidine alkaloids 1,4-dideoxy-1,4-imino-d-galactitol and its diastereoisomer 1,4-dideoxy-1,4-imino-d-glucitol is described, starting from a common optically active precursor. The key step in our approach was the double diastereoselection in the asymmetric dihydroxylation of chiral vinyl azido alcohols, obtained by means of two different regio- and stereoselective nucleophilic openings of the corresponding chiral vinyl epoxide. Copyright © 2016 Elsevier Ltd. All rights reserved.

Citation

Giuliana Righi, Emanuela Mandic', Carla Sappino, Ergys Dema, Paolo Bovicelli. Asymmetric routes toward polyhydroxylated pyrrolidines: Synthesis of 1,4-dideoxy-1,4-imino-d-galactitol and 1,4-dideoxy-1,4-imino-d-glucitol. Carbohydrate research. 2016 Nov 29;435:100-105