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Asymmetric Synthesis of a Pyrrolizidinone‐Based hNK1 Antagonist through Reductive Ring Contraction of a Six‐Membered Cyclic Nitronateстатья
Информация о цитировании статьи получена из
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Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 20 февраля 2024 г.
- Авторы: Okladnikov Ilya V., Boyko Yaroslav D., Nelyubina Yulia V., Ioffe Sema L., Sukhorukov Alexey Yu
- Журнал: European Journal of Organic Chemistry
- Том: 2022
- Номер: 41
- Год издания: 2022
- Издательство: John Wiley & Sons Ltd.
- Местоположение издательства: United Kingdom
- Номер статьи: e202200796
- DOI: 10.1002/ejoc.202200796
- Аннотация: A concise seven-step asymmetric synthesis of MSD's potent hNK1 antagonist containing a pyrrolizidinone core bearing two fluorine-substituted aryl groups was developed. The pyrrolizidinone unit was constructed by reductive recyclization of a properly functionalized cyclic nitronate, which was assembled by stereoselective [4+2]-cycloaddition of a nitroalkene with a vinyl ether bearing a Whitesell's chiral auxiliary group. The configuration of the hNK1 antagonist, which was previously suggested based on bioactivity data, was confirmed by X-ray analysis. The crystal structure features multiple weak interactions involving fluorine atoms that are also found in a complex with the hNK1 receptor simulated by molecular docking.
- Добавил в систему: Сухоруков Алексей Юрьевич