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Título

Synthesis of morpholine‐based analogues of (−)‐zampanolide and their biological activity

AutorBold, Christian Paul; Gut, Melanie; Schürmann, Jasmine; Lucena-Agell, Daniel CSIC ORCID ; Gertsch, Jürg; Díaz, José Fernando CSIC ORCID ; Altmann, Karl-Heinz
Palabras claveMacrocyclization
Stereoselective aza aldolreaction
Structure–activity relationships
Total synthesis
Zampanolide
Fecha de publicación1-abr-2021
EditorJohn Wiley & Sons
CitaciónChemistry - A European Journal 27 (19) 5936-5943 (2021)
ResumenWe 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.
Descripción9 p.-1 fig.-1 tab.-6 schem.
Versión del editorhttps://doi.org/10.1002/chem.202003996
URIhttp://hdl.handle.net/10261/236573
DOI10.1002/chem.202003996
ISSN0947-6539
E-ISSN1521-3765
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