Chemical Modification of Plant Alkaloids. 8. Stereocontrolled T-Reactions of (1R,5S,12S)-Tetrahydrocytisine Derivatives

New heterocyclic quinolizidine systems were prepared from (1R,5S,12S)-tetrahydrocytisine. The synthetic scheme included arylation of tetrahydrocytisine by 2-fluoro-5-nitrobenzaldehyde and condensation of the resulting aldehyde with 1,3-dimethylbarbituric acid. The Knoevenagel intermediate obtained from the condensation was cyclized by a T-reaction to give two spirocyclic products as a derivative with the lupanine skeleton and its regioisomer with the 11,15-diazapentacyclo[11.7.1.02,11.05,10.015,20]heneicosane skeleton. The cyclization occurred highly stereoselectively. The structures of the products were proven using NMR and X-ray crystal structure analyses. © 2018, Springer Science+Business Media, LLC, part of Springer Nature.

Авторы
Krasnov K.A.1 , Kartsev V.G. 2 , Dobrokhotova E.V. 3 , Kultyshkina E.K. 3 , Chernikova N.Y. 3 , Dorovatovskii P.V.4 , Zubavichus Y.V.4 , Khrustalev V.N. 3, 4
Номер выпуска
4
Язык
Английский
Страницы
739-744
Статус
Опубликовано
Том
54
Год
2018
Организации
  • 1 Institute of Toxicology, Federal Medico-Biological Agency of Russia, 1 Bekhtereva St., St. Petersburg, 192019, Russian Federation
  • 2 Interbioscreen Ltd., 8 Institutskii Prosp., Chernogolovka, Moscow Region 142432, Russian Federation
  • 3 People’s Friendship University of Russia, 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation
  • 4 National Research Center Kurchatov Institute, 1 Akad. Kurchatova Sq., Moscow, 123182, Russian Federation
Ключевые слова
(1R,5S,12S)-tetrahydrocytisine; 1,3-dimethylbarbituric acid; hydride shift; lupanine derivative; stereocontrolled synthesis; T-reaction
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/6558/