Issue 40, 2019

The synthesis of solasodine F-homo-analogues

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

Supplementary files

Article information

Article type
Paper
Submitted
28 Aug 2019
Accepted
26 Sep 2019
First published
28 Sep 2019

Org. Biomol. Chem., 2019,17, 9050-9058

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements