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 epoxide
2016
1,4-Dideoxy-1,4-imino-D-galactitol; 1,4-Dideoxy-1,4-imino-D-glucitol; asymmetric dihydroxylation; iminosugar; polyhydroxylated pyrrolidines; analytical chemistry; biochemistry; organic chemistry
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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. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - 435:(2016), pp. 100-105. [10.1016/j.carres.2016.09.018]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/933890
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