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Título: | Synthesis of morpholine‐based analogues of (−)‐zampanolide and their biological activity |
Autor: | Bold, Christian Paul; Gut, Melanie; Schürmann, Jasmine; Lucena-Agell, Daniel CSIC ORCID ; Gertsch, Jürg; Díaz, José Fernando CSIC ORCID ; Altmann, Karl-Heinz | Palabras clave: | Macrocyclization Stereoselective aza aldolreaction Structure–activity relationships Total synthesis Zampanolide |
Fecha de publicación: | 1-abr-2021 | Editor: | John Wiley & Sons | Citación: | Chemistry - A European Journal 27 (19) 5936-5943 (2021) | Resumen: | We describe the convergent synthesis of threeprototypical examples of a new class of analogues of thecomplex, cytotoxic marine macrolide ()-zampanolide thatincorporate an embedde d N-substituted morpholine moietyin place of the natural tetrahydropyran ring. The final con-struction of the macrolactone core was based on a high-yielding intramolecular HWE olefination, while the hemiami-nal-linked side chain was elaborated through a stereoselec-tive, BINAL-H-mediated addition of (Z,E)-sorbamide to a macrocyclic aldehyde precursor. The synthesis of the commonfunctionalized morpholine building block involved two con-secutive epoxide openings with tosylamide and the productof the first opening reaction, respectively, as nucleophiles. Ofthe three morpholino-zampanolides investigated, the N -acetyl and the N-benzoyl derivatives both exhibited nano-molar antiproliferative activity, thus being essentially equipo-tent with the natural product. In contrast, the activity of theN-tosyl derivative was significantly reduced. | Descripción: | 9 p.-1 fig.-1 tab.-6 schem. | Versión del editor: | https://doi.org/10.1002/chem.202003996 | URI: | http://hdl.handle.net/10261/236573 | DOI: | 10.1002/chem.202003996 | ISSN: | 0947-6539 | E-ISSN: | 1521-3765 |
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