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SM ISO690:2012 ZHABINSKII, Vladimir, HURSKI, Alaksiej, LAKTSEVICH-ISKRYK, Marharyta, KUKEL, Aliaksandr, LIUBINA, Aliaksandra, BARADZENKA, Aliona, STRALTSOVA, Darya, DEMIDCHIK, Vadim, DRASAR, Pavel, KHRIPACH, Vladimir. C-H functionalization of brassinosteroids. In: Achievements and perspectives of modern chemistry, 9-11 octombrie 2019, Chişinău. Chisinau, Republic of Moldova: Tipografia Academiei de Ştiinţe a Moldovei, 2019, p. 248. ISBN 978-9975-62-428-2. |
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Achievements and perspectives of modern chemistry 2019 | |
Conferința "International Conference "Achievements and perspectives of modern chemistry"" Chişinău, Moldova, 9-11 octombrie 2019 | |
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Pag. 248-248 | |
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Brassinosteroids are hormones that regulate numerous biological processes in plantsincluding growth, reproduction and resistance to stresses [1]. These steroids are available only synthetically and their preparation is a laborious task. Nevertheless, such brassinosteroids as 24-epibrassinolide and 24-epicastasterone are used in agrochemistry and efficient protocols for their preparation on kilograms scale have been developed. Conjugates of brassinosteroids with fluorescent dyes are demanded in chemical biology for visualization of biochemical processes. An important issue in the design of the conjugates is that after the chemical modification, biological activity of a modified steroid should be similar to that of the parent molecule. As far as functional groups in brassinosteroids are responsible for biological activity, we decided to prepare conjugates in which a linker would be connected to the hydrocarbon skeleton of the molecule. Although total synthesis of steroids with a modified core still remains a challenging task, significant progress in the regioselective modification of complex molecules by means of direct C-H bond functionalization has been achieved recently [2]. Two regioselective C-H activation-based methods for derivatization of readily available 24-epibrassinolide and 24-epicastasterone will be presented in the current communication. Our first approach is based on the rhodium-catalyzed C-H amination that enabled the preparation of C15-functionalized brassinosteroids [3]. An alternative method of hydroxyl-directed 1,5-hydrogen atom transfer was utilized to prepare C19-modified 24-epicastasterone. All of the obtained derivatives of brassinosteroids were successfully transformed to the conjugates with BODIPY dyes.formula |
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