247230-49-5Relevant academic research and scientific papers
Stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants
Schiess, Raphael,Gertsch, Juerg,Schweizer, W. Bernd,Altmann, Karl-Heinz
supporting information; experimental part, p. 1436 - 1439 (2011/05/13)
A general strategy has been devised for the stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants thereof, which relies on late stage introduction of the heterocycle through Wittig olefination of ketone 14. Formation of the macrocycle was achieved through RCM-based ring closure and introduction of the cyclopropane moiety involved a highly selective Charette cyclopropanation of allylic alcohol 7.
SYNTHESIS OF EPOTHILONES, INTERMEDIATES THERETO, ANALOGUES AND USES THEREOF
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Page 120, (2008/06/13)
The present invention provides compounds of formula (I): as described generally and in classes and subclasses herein. The present invention additionally provides pharmaceutical compositions comprising compounds of formula (I) and provides methods of treating cancer comprising administering a compound of formula (I).
Synthesis, structure proof, and biological activity of epothilone cyclopropanes.
Johnson,Kim,Bifano,DiMarco,Fairchild,Gougoutas,Lee,Long,Tokarski,Vite
, p. 1537 - 1540 (2007/10/03)
[structure--see text] A semisynthetic route to epothilone cyclopropanes from epothilones A and B is described. Of significance, the deoxygenation of the 12, 13-epoxide to give the corresponding olefin was achieved with high efficiency. The title compounds (8, 9) were active in both tubulin polymerization and cytotoxicity assays, which is in direct contrast to a previously published report. These results provide further evidence that the role of the 12,13-epoxide of epothilones is largely conformational and argue against some of the current pharmacophore models.
