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 stereo selective nucleophilic openings of the corresponding chiral vinyl epoxide. (C) 2016 Elsevier Ltd. All rights reserved.

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;Bovicelli Paolo
2016

Abstract

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 stereo selective nucleophilic openings of the corresponding chiral vinyl epoxide. (C) 2016 Elsevier Ltd. All rights reserved.
2016
Iminosugar
Polyhydroxylated pyrrolidines
1,4-Dideoxy-1,4-imino-D-galactitol
1,4-Dideoxy-1,4-imino-D-glucitol
Asymmetric dihydroxylation
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.14243/326785
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