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A Practical Synthesis of Betulonic Acid Using Selective Oxidation of Betulin on Aluminium Solid Support
Department of Pharmaceutical Chemistry, Nizhny Novgorod State Medical Academy, Minin sq. 10/1, Nizhny Novgorod 603-000, Russia
Department of Chemistry, N.P. Ogarev Mordovian State University, Mironov St. 3-274, Saransk 430-005, Russia
Department of Chemistry, Nizhny Novgorod State University, Kuibishev St. 17-25, Nizhny Novgorod 603-950, Russia
* Author to whom correspondence should be addressed.
Received: 10 August 2012; in revised form: 23 September 2012 / Accepted: 24 September 2012 / Published: 9 October 2012
Abstract: The room temperature oxidation of betulin by Cr(VI) compounds in aqueous acetone on solid supports such as alumina, zeolites and silica gel has been studied. The oxidation on alumina support leaded to a single product—betulonic acid—in quantitative yield. One hundred percent selective oxidation during 30 min of betulin up to betulonic aldehyde was determined when silica gel support was used. The oxidation of betulin using zeolites as a support gives a mixture of betulonic acid and aldehyde in a 2:1 ratio. It is proposed the selective oxidation up to betulonic acid is due to the influence of Al3+-ions.
Keywords: oxidation on alumina; betulin; betulonic acid; protection of double bond by Al3+-ions
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Melnikova, N.; Burlova, I.; Kiseleva, T.; Klabukova, I.; Gulenova, M.; Kislitsin, А.; Vasin, V.; Tanaseichuk, B. A Practical Synthesis of Betulonic Acid Using Selective Oxidation of Betulin on Aluminium Solid Support. Molecules 2012, 17, 11849-11863.
Melnikova N, Burlova I, Kiseleva T, Klabukova I, Gulenova M, Kislitsin А, Vasin V, Tanaseichuk B. A Practical Synthesis of Betulonic Acid Using Selective Oxidation of Betulin on Aluminium Solid Support. Molecules. 2012; 17(10):11849-11863.
Melnikova, Nina; Burlova, Irina; Kiseleva, Tatiana; Klabukova, Irina; Gulenova, Marina; Kislitsin, Аleksey; Vasin, Viktor; Tanaseichuk, Boris. 2012. "A Practical Synthesis of Betulonic Acid Using Selective Oxidation of Betulin on Aluminium Solid Support." Molecules 17, no. 10: 11849-11863.