Synthesis of triterpenoid-based 1,2,4-trioxolanes and 1,2,4-dioxazolidines by ozonolysis of allobetulin derivatives |
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| Authors: | Oxana B Kazakova Dmitri V KazakovEmil Yu Yamansarov Natal’ya I MedvedevaGenrikh A Tolstikov Kyrill Yu SuponitskyDmitri E Arkhipov |
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| Institution: | a Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71, pr. Oktyabrya, 450054 Ufa, Russian Federation
b A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28, Vavilov St., 119991 Moscow, Russian Federation |
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| Abstract: | Oxidation of allobetulin derivatives with ozone results in good isolated yields of 1,2,4-trioxolanes and stable 1,2,4-dioxazolidines. Individual 3R,5R and 3S,5S diastereoisomers of allobetulin secondary ozonides were isolated and their structures confirmed by X-ray crystallographic analysis. Remarkable diastereoselectivity with formation of only the (3S,5S)-configured peroxides was observed during the oxidation of 1,5-di-O-methoxyoximinoallobetulin to dioxazolidines. |
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| Keywords: | Natural products Triterpenoids Betulin Antimalarials Peroxides 1 2 4-Trioxolanes 1 2 4-Dioxazolidines Ozonolysis |
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