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Title

The Total Synthesis and Biological Properties of the Cytotoxic Macrolide FD-891 and Its Non-Natural (Z)-C12 Isomer

AuthorsGarcía-Fortanet, Jorge Isabel Barasoain; Murga, Juan; Carda, Miguel; Marco, J. Alberto; Matesanz, Ruth ; Díaz, José Fernando ; Barasoain, Isabel
KeywordsAldol reaction
allylation
antitumor agents
lactones
olefination
tubulin binding
Issue Date15-Jun-2007
PublisherWiley-VCH
CitationChemistry - A European Journal 13(18):5060–5074(2007)
AbstractA 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
Description15 páginas, 1 figura, 1 tabla, 10 esquemas -- PAGS nros. 5060-5074
Publisher version (URL)http://dx.doi.org/10.1002/chem.200700342
URIhttp://hdl.handle.net/10261/63232
DOI10.1002/chem.200700342
ISSN0947-6539
E-ISSN1521-3765
Appears in Collections:(CIB) Artículos
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