Chemical Modification of Plant Alkaloids. 8. Stereocontrolled T-Reactions of (1R,5S,12S)-Tetrahydrocytisine Derivatives Full article
Journal |
Chemistry of Natural Compounds
ISSN: 0009-3130 , E-ISSN: 1573-8388 |
||||||||
---|---|---|---|---|---|---|---|---|---|
Output data | Year: 2018, Volume: 54, Number: 4, Pages: 739-744 Pages count : 6 DOI: 10.1007/s10600-018-2459-z | ||||||||
Tags | (1R,5S,12S)-tetrahydrocytisine; 1,3-dimethylbarbituric acid; hydride shift; lupanine derivative; stereocontrolled synthesis; T-reaction | ||||||||
Authors |
|
||||||||
Affiliations |
|
Abstract:
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.
Cite:
Krasnov K.A.
, Kartsev V.G.
, Dobrokhotova E.V.
, Kultyshkina E.K.
, Chernikova N.Y.
, Dorovatovskii P.V.
, Zubavichus Y.V.
, Khrustalev V.N.
Chemical Modification of Plant Alkaloids. 8. Stereocontrolled T-Reactions of (1R,5S,12S)-Tetrahydrocytisine Derivatives
Chemistry of Natural Compounds. 2018. V.54. N4. P.739-744. DOI: 10.1007/s10600-018-2459-z WOS Scopus РИНЦ
Chemical Modification of Plant Alkaloids. 8. Stereocontrolled T-Reactions of (1R,5S,12S)-Tetrahydrocytisine Derivatives
Chemistry of Natural Compounds. 2018. V.54. N4. P.739-744. DOI: 10.1007/s10600-018-2459-z WOS Scopus РИНЦ
Original:
Краснов К.А.
, Карцев В.Г.
, Доброхотова Е.В.
, Култышкина Е.К.
, Черникова Н.Ю.
, Дороватовский П.В.
, Зубавичус Я.В.
, Хрусталев В.Н.
Химическая модификация растительных алкалоидов. 8. Стереонаправленные Т-реакции производного (1R,5S,12S)-тетрагидроцитизина
Химия природных соединений. 2018. №4. С.624-629. РИНЦ
Химическая модификация растительных алкалоидов. 8. Стереонаправленные Т-реакции производного (1R,5S,12S)-тетрагидроцитизина
Химия природных соединений. 2018. №4. С.624-629. РИНЦ
Dates:
Submitted: | Jan 23, 2018 |
Published print: | Jul 1, 2018 |
Published online: | Jul 25, 2018 |
Identifiers:
Web of science | WOS:000440423000029 |
Scopus | 2-s2.0-85050684072 |
Elibrary | 35738442 |
Chemical Abstracts | 2018:1423013 |
OpenAlex | W2883541272 |
Citing:
Пока нет цитирований