899798-80-2Relevant articles and documents
Synthesis and structure-activity relationship study of FD-891: Importance of the side chain and C8-C9 epoxide for cytotoxic activity against cancer cells
Itagaki, Tomohiro,Kawamata, Ayano,Takeuchi, Miho,Hamada, Keisuke,Iwabuchi, Yoshiharu,Eguchi, Tadashi,Kudo, Fumitaka,Usui, Takeo,Kanoh, Naoki
, p. 287 - 293 (2016/05/09)
Unified synthesis of FD-891 analogs and their structure-activity relationship are described. By using stereoselective allylation/crotylation and Evans aldol chemistry, six side-chain fragments having different length and terminus were synthesized. These f
The total synthesis and biological properties of the cytotoxic macrolide FD-891 and its non-natural (Z)-C12 isomer
Garcia-Fortanet, Jorge,Murga, Juan,Carda, Miguel,Marco, J. Alberto,Matesanz, Ruth,Diaz, J. Fernando,Barasoain, Isabel
, p. 5060 - 5074 (2008/02/11)
A total, stereoselective synthesis of the naturally occurring, cytotoxic macrolide FD-891 and of its non-natural (Z)-C12 isomer is described. Three fragments of the main carbon chain were stereoselectively prepared by using asymmetric aldol and allylation reactions as the key steps. The molecule was then assembled by using two Julia-Kocienski olefinations to connect the three fragments and a Yamaguchi reaction to close the macrolactone ring. Some specific biological properties (cytotoxicity, binding to tubulin) have been determined for both macrolides. The E configuration of the C12-C13 olefinic bond seems to be an important feature in determining the cytotoxicity but the precise biological mechanism of the latter still remains to be cleared.
Stereoselective synthesis of the cytotoxic macrolide FD-891
Garcia-Fortanet, Jorge,Murga, Juan,Carda, Miguel,Marco, J. Alberto
, p. 2695 - 2698 (2007/10/03)
A total synthesis of the naturally occurring, cytotoxic macrolide FD-891 is described. Three fragments were first stereoselectively constructed using mainly asymmetric aldol and allylation reactions. The complete framework was then assembled using two Jul