4860-15-5Relevant academic research and scientific papers
Copper-catalyzed 1,3-dipolar cycloaddition reaction of spirosolanederived azide for the preparation of modified solasodine alkaloid
Finke, Anastasiya O.,Mironov, Maxim E.,Skorova, Anna B.,Shults, Elvira E.
, p. 411 - 416 (2018)
[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.
Some observations on solasodine reactivity
Jastrzebska, Izabella,Morzycki, Jacek W.
, p. 13 - 17 (2017)
This article presents new transformations of solasodine – a representative steroid alkaloid sapogenin from the Solanum family. Oxidation of N,O-diacetylated solasodine with either NaNO2/BF3·Et2O or t-BuONO/BF3·Et2O resulted in partial degradation of the side chain to (20S)-3β-acetoxypregn-5-ene-20,16β-carbolactone (vespertilin acetate). The same starting compound when treated with TMSOTf afforded the corresponding pseudosapogenin after aqueous work-up. However, when the crude reaction mixture was directly subjected to purification on a silica gel column, efficient autoxidation to pregna-5,16-dien-3β-ol-20-one acetate was observed. One-step synthesis of this important drug intermediate from spirosolan alkaloids may be potentially exploited for large-scale production of steroid hormones.
