Herein the total synthesis of the pyrrolidine alkaloids 1,4-dideoxy-1,4-imino-D-galactitol and its diaste-reoisomer 1,4-dideoxy-1,4-imino-D-glucitol is described, starting from a common optically active pre-cursor. The key step in our approach was the double diastereoselection in the asymmetricdihydroxylation of chiral vinyl azido alcohols, obtained by means of two different regio- and stereo-selective nucleophilic openings of the corresponding chiral vinyl epoxide
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. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - 435:(2016), pp. 100-105. [10.1016/j.carres.2016.09.018]
Asymmetric routes toward polyhydroxylated pyrrolidines: Synthesis of 1,4-dideoxy-1,4-imino-D-galactitol and 1,4-dideoxy-1,4-imino-D-glucitol
MANDIC', EMANUELA;SAPPINO, CARLA;
2016
Abstract
Herein the total synthesis of the pyrrolidine alkaloids 1,4-dideoxy-1,4-imino-D-galactitol and its diaste-reoisomer 1,4-dideoxy-1,4-imino-D-glucitol is described, starting from a common optically active pre-cursor. The key step in our approach was the double diastereoselection in the asymmetricdihydroxylation of chiral vinyl azido alcohols, obtained by means of two different regio- and stereo-selective nucleophilic openings of the corresponding chiral vinyl epoxideFile | Dimensione | Formato | |
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