Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid

Anastasiya O. Finke, Maxim E. Mironov, Anna B. Skorova, Elvira E. Shults

Результат исследования: Научные публикации в периодических изданияхстатья

1 Цитирования (Scopus)

Аннотация

[Figure not available: see fulltext.] Modification of the steroidal alkaloid solasodine was performed by introduction of 1,2,3-triazolyl substituents at the С-6 atom of spirosolane ring system. The azidolysis of 5,6α-epoxysolasodine diacetate, formed as the major product during epoxidation of solasodine diacetate by the action of sodium azide in DMF in the presence of ammonium chloride, proceeded through the formation of 6β-azido-5α-hydroxysolasodine diacetate. The newly obtained azide was used in reactions with terminal alkynes in the presence of copper(I) bromide and N,N-diisopropylethylamine in DMF to synthesize the respective (22R,25R)-N,O-diacetyl-6β-[4-aryl-1,2,3-triazol-1-yl]-5α-hydroxyspirosolanes.

Язык оригиналаанглийский
Страницы (с-по)411-416
Число страниц6
ЖурналChemistry of Heterocyclic Compounds
Том54
Номер выпуска4
DOI
СостояниеПринято в печать - 8 июн 2018

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