• This record comes from PubMed

Total Synthesis of ent-Pregnanolone Sulfate and Its Biological Investigation at the NMDA Receptor

. 2018 Feb 16 ; 20 (4) : 946-949. [epub] 20180124

Language English Country United States Media print-electronic

Document type Journal Article, Research Support, Non-U.S. Gov't

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 organocatalytic Robinson annulation. A new method for the construction of the cyclopentane D-ring consisting of CuI-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.

References provided by Crossref.org

Find record

Citation metrics

Loading data ...

Archiving options

Loading data ...