0489699 - ÚOCHB 2019 RIV US eng J - Journal Article
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
R&D Projects: GA ČR(CZ) GBP304/12/G069; GA TA ČR(CZ) TE01020028; GA MZd(CZ) NV15-29370A
Grant - others:AV ČR(CZ) MSM200111601
Program: Program na podporu mezinárodní spolupráce začínajících výzkumných pracovníků
Institutional support: RVO:61388963 ; RVO:67985823
Keywords : Robinson annulation * organocatalysis * radical cyclizations * conjugate addition * Saegusa oxidation
OECD category: Organic chemistry
Impact factor: 6.555, year: 2018
DOI: https://doi.org/10.1021/acs.orglett.7b03838

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.

Permanent Link: http://hdl.handle.net/11104/0284065