Solasodine derivatives continue to be attractive targets for synthetic chemists due to their interesting biological properties. Herein, we report a concise synthesis of solasodine analogues containing the seven-membered F ring from diosgenin. The key intermediate in the synthesis of 26a-homosolane derivatives was 26-cyanopseudodiosgenin. After reduction of the cyano group, the seven-membered ring was closed with MgBr2·Et2O to yield 26a-homosolanes as a mixture of 22R and 22S epimers. The acylation of the obtained mixture led to the diastereomerically pure 22S N-acylated 26a-homosolasodine derivatives. Moreover, we describe one-step protocol for stereoselective synthesis of 22R-cyanofurostane by treatment of diosgenin with TMSCN/BF3·Et2O.

Institute of Chemistry University of Białystok K Ciołkowskiego 1 K 15 245 Białystok Poland

Laboratory of Growth Regulators Faculty of Science Palacký University and Institute of Experimental Botany of the Czech Academy of Sciences Šlechtitelů 27 CZ 78371 Olomouc Czech Republic

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