| Full text | |
| Author(s): |
Palo-Nieto, Carlos
[1]
;
Sau, Abhijit
[1]
;
Jeanneret, Robin
[1]
;
Payard, Pierre-Adrien
[2]
;
Salame, Aude
[2]
;
Martins-Teixeira, Maristela Braga
[3]
;
Carvalho, Ivone
[3]
;
Grimaud, Laurence
[2]
;
Galan, M. Carmen
[1]
Total Authors: 9
|
| Affiliation: | [1] Univ Bristol, Sch Chem, Bristol BS8 3TS, Avon - England
[2] Sorbonne Univ, Ecole Normale Super, CNRS, Lab Biomol LBM, F-75005 Paris - France
[3] Univ Sao Paulo, Sch Pharmaceut Sci Ribeirao Preto, BR-14040903 Monte Alegre do Sul - Brazil
Total Affiliations: 3
|
| Document type: | Journal article |
| Source: | ORGANIC LETTERS; v. 22, n. 5, p. 1991-1996, MAR 6 2020. |
| Web of Science Citations: | 1 |
| Abstract | |
We demonstrate that tuning the reactivity of Cu by the choice of oxidation state and counterion leads to the activation of both ``armed{''} and ``disarmed{''} type glycals toward direct glycosylation leading to the alpha-stereoselective synthesis of deoxyglycosides in good to excellent yields. Mechanistic studies show that Cu-I is essential for effective catalysis and stereocontrol and that the reaction proceeds through dual activation of both the enol ether as well as the OH nucleophile. (AU) | |
| FAPESP's process: | 16/21194-6 - Synthesis of 2-deoxyglycoside derivatives of anthracyclines |
| Grantee: | Maristela Braga Martins Teixeira |
| Support Opportunities: | Scholarships abroad - Research Internship - Doctorate |