Total Synthesis of ent-Pregnanolone Sulfate and Its Biological Investigation at the NMDA Receptor
Jazyk angličtina Země Spojené státy americké Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
- MeSH
- cyklizace MeSH
- molekulární struktura MeSH
- pregnanolon chemická syntéza MeSH
- receptory N-methyl-D-aspartátu MeSH
- sírany MeSH
- stereoizomerie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- pregnanolon MeSH
- receptory N-methyl-D-aspartátu MeSH
- sírany MeSH
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.
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