Stereoselective synthesis and biological evaluation of D-fagomine, D-3-epi-fagomine and D-3,4-epi-fagomine analogs from D-glyceraldehyde acetonide as a common building block

The stereoselective synthesis of D-fagomine, D-3-epi-fagomine, and D-3-epi-fagomine analogs starting from readily available D-glyceraldehyde acetonide has been achieved. The synthesis involves diastereoselective anti-vinylation of its homoallylimine, ring-closing metathesis, and stereoselective epox...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-12, Vol.10 (46), p.9278-9286
Main Authors: Díez, J Alberto, Gálvez, José A, Díaz-de-Villegas, María D, Badorrey, Ramón, Bartholomew, Barbara, Nash, Robert J
Format: Article
Language:English
Subjects:
Glyceraldehyde - analogs & derivatives
Glyceraldehyde - chemistry
Hydroxylation
Imino Pyranoses - chemical synthesis
Magnetic Resonance Spectroscopy
Molecular Chaperones - chemical synthesis
Molecular Structure
Stereoisomerism
Structure-Activity Relationship
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The stereoselective synthesis of D-fagomine, D-3-epi-fagomine, and D-3-epi-fagomine analogs starting from readily available D-glyceraldehyde acetonide has been achieved. The synthesis involves diastereoselective anti-vinylation of its homoallylimine, ring-closing metathesis, and stereoselective epoxidation followed by regioselective ring-opening or stereoselective dihydroxylation. The lack of a strong activity as glycosidase inhibitors of these compounds could be advantageous for their therapeutic use as chaperones.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob26732b