Regioselective C–H Amination of Lupane-Type Triterpenoids
Balticum Organicum Syntheticum 2024: Abstract Book 2024
Vladislavs Kroškins, Jevgeņija Lugiņina, Māris Turks

Betulin and betulinic acid are lupane-type secondary metabolites found in birch bark. These triterpenoids and their derivatives are known for their remarkable antitumor, antidiabetic, anti-inflammatory and antiviral properties. Among many possible functionalization possibilities, the C–H activation is underdeveloped in this compound class. Hence, we present here C(16) and C(22) C–H amination followed by functional group transformation that provides heteroatom containing triterpenoid derivatives with better solubility profile. Sulfamate ester 2 was obtained in few steps from betulin (1) and following C-H amination reaction proceeds in the presence of rhodium catalyst, forming oxathiazinane 3, which is versatile precursor for various ring-opening reactions.


Keywords
pentacikliskie triterpenoīdi, pārejas metālu katalīze, C-H aktivācija
Hyperlink
https://boschem.eu/bos2024/wp-content/uploads/sites/5/2024/07/BOS2024_Abstract-Book-SMALL1.pdf

Kroškins, V., Lugiņina, J., Turks, M. Regioselective C–H Amination of Lupane-Type Triterpenoids. In: Balticum Organicum Syntheticum 2024: Abstract Book, Latvia, Riga, 7-10 July, 2024. Riga: 2024, pp.81-81.

Publication language
English (en)
The Scientific Library of the Riga Technical University.
E-mail: uzzinas@rtu.lv; Phone: +371 28399196