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Issue 40, 2019
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The synthesis of solasodine F-homo-analogues

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Abstract

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.

Graphical abstract: The synthesis of solasodine F-homo-analogues

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Publication details

The article was received on 28 Aug 2019, accepted on 26 Sep 2019 and first published on 28 Sep 2019


Article type: Paper
DOI: 10.1039/C9OB01888C
Org. Biomol. Chem., 2019,17, 9050-9058

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    The synthesis of solasodine F-homo-analogues

    U. Kiełczewska, J. W. Morzycki, L. Rárová and A. Wojtkielewicz, Org. Biomol. Chem., 2019, 17, 9050
    DOI: 10.1039/C9OB01888C

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