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Asymmetric routes toward polyhydroxylated pyrrolidines: Synthesis of 1,4-dideoxy-1,4-imino-d-galactitol and 1,4-dideoxy-1,4-imino-d-glucitol
- Righi, Giuliana, Mandic', Emanuela, Sappino, Carla, Dema, Ergys, Bovicelli, Paolo
- Carbohydrate research 2016 v.435 pp. 100-105
- alcohols, dihydroxylation, pyrrolidine alkaloids, pyrrolidines, stereochemistry
- 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.