Počet záznamů: 1
Total Synthesis of ent-Pregnanolone Sulfate and Its Biological Investigation at the NMDA Receptor
- 1.0489699 - ÚOCHB 2019 RIV US eng J - Článek v odborném periodiku
Kapras, Vojtěch - Vyklický, Vojtěch - Buděšínský, Miloš - Císařová, I. - Vyklický ml., Ladislav - Chodounská, Hana - Jahn, Ullrich
Total Synthesis of ent-Pregnanolone Sulfate and Its Biological Investigation at the NMDA Receptor.
Organic Letters. Roč. 20, č. 4 (2018), s. 946-949. ISSN 1523-7060. E-ISSN 1523-7052
Grant CEP: GA ČR(CZ) GBP304/12/G069; GA TA ČR(CZ) TE01020028; GA MZd(CZ) NV15-29370A
Grant ostatní: AV ČR(CZ) MSM200111601
Program: Program na podporu mezinárodní spolupráce začínajících výzkumných pracovníků
Institucionální podpora: RVO:61388963 ; RVO:67985823
Klíčová slova: Robinson annulation * organocatalysis * radical cyclizations * conjugate addition * Saegusa oxidation
Obor OECD: Organic chemistry
Impakt faktor: 6.555, rok: 2018
A unique asymmetric total synthesis of the unnatural enantiomer of pregnanolone, as well as a study of its biological activity at the NMDA receptor, is reported. The asymmetry is introduced by a highly atom-economic organo-catalytic Robinson annulation. A new method for the construction of the cyclopentane D-ring consisting of Cu-I-catalyzed conjugate addition and oxygenation followed by thermal cyclization employing the persistent radical effect was developed. ent-Pregnanolone sulfate is surprisingly only 2.6-fold less active than the natural neurosteroid.
Trvalý link: http://hdl.handle.net/11104/0284065
Počet záznamů: 1