Publikace na Přírodovědecká fakulta |
2018
Abstrakt
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.