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
J Alberto Díez
1
,
José A Gálvez
1
,
María D. Díaz-de-Villegas
1
,
Ramón Badorrey
1
,
Barbara Bartholomew
2
,
ROBERT M. NASH
2
1
2
Phytoquest Limited, Plas Gogerddan, Aberystwyth, Ceredigion, UK
|
Publication type: Journal Article
Publication date: 2012-10-11
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
23104470
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
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.
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Total citations:
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Citations from 2024:
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(11.11%)
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Díez J. A. et al. 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 // Organic and Biomolecular Chemistry. 2012. Vol. 10. No. 46. p. 9278.
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Díez J. A., Gálvez J. A., Díaz-de-Villegas M. D., Badorrey R., Bartholomew B., NASH R. M. 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 // Organic and Biomolecular Chemistry. 2012. Vol. 10. No. 46. p. 9278.
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RIS
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TY - JOUR
DO - 10.1039/c2ob26732b
UR - https://doi.org/10.1039/c2ob26732b
TI - 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
T2 - Organic and Biomolecular Chemistry
AU - Díez, J Alberto
AU - Gálvez, José A
AU - Díaz-de-Villegas, María D.
AU - Badorrey, Ramón
AU - Bartholomew, Barbara
AU - NASH, ROBERT M.
PY - 2012
DA - 2012/10/11
PB - Royal Society of Chemistry (RSC)
SP - 9278
IS - 46
VL - 10
PMID - 23104470
SN - 1477-0520
SN - 1477-0539
ER -
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BibTex (up to 50 authors)
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@article{2012_Díez,
author = {J Alberto Díez and José A Gálvez and María D. Díaz-de-Villegas and Ramón Badorrey and Barbara Bartholomew and ROBERT M. NASH},
title = {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},
journal = {Organic and Biomolecular Chemistry},
year = {2012},
volume = {10},
publisher = {Royal Society of Chemistry (RSC)},
month = {oct},
url = {https://doi.org/10.1039/c2ob26732b},
number = {46},
pages = {9278},
doi = {10.1039/c2ob26732b}
}
Cite this
MLA
Copy
Díez, J. Alberto, et al. “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.” Organic and Biomolecular Chemistry, vol. 10, no. 46, Oct. 2012, p. 9278. https://doi.org/10.1039/c2ob26732b.