Synthesis of Novel Lupane Triterpenoid-Indazolone Hybrids with Oxime Ester Linkage

Proceedings of the National Academy of Sciences of Belarus. Series of Chemical Sciences 2016
Tatyana S. Khlebnicova, Yuri A. Piven, Daina Zicāne, Inese Mieriņa, Uldis Peipiņš, Māris Turks

An efficient protocol for the synthesis of novel lupane triterpenoid-indazolone hybrids with oxime ester linkage has been developed from naturally accessible precursor betulin. For the first time a series of betulonic acid-indazolone hybrids have been synthesized via an acylation of corresponding 6,7-dihydro-1H-indazol-4(5H)-one oximes with betulonic acid chloride. Diastereoselective reduction of the obtained betulonic acid conjugates with NaBH4 resulted in a formation of betulinic acid-indazolone hybrids in excellent yields. The configuration of the key compounds has been fully established by X-ray and 2D NMR analysis.

Keywords
lupane triterpenoid-indazolone hybrids

Khlebnicova, T., Piven, Y., Zicāne, D., Mieriņa, I., Peipiņš, U., Turks, M. Synthesis of Novel Lupane Triterpenoid-Indazolone Hybrids with Oxime Ester Linkage. In: Proceedings of the National Academy of Sciences of Belarus. Series of Chemical Sciences, Belarus, Minsk, 4-7 September, 2016. Minsk: Belaruskaya Navuka Publishing House, 2016, pp.105-106. ISSN 0002-3590.

Publication language
English (en)