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| Título: | A method for the stereoselective construction of the hemiaminal center in zampanolides |
Autor: | Brütsch, Tobias M.; Berardozzi, Simone; Rothe, Marlene L.; Redondo-Horcajo, Mariano CSIC ORCID ; Díaz, José Fernando CSIC ORCID ; Altmann, Karl-Heinz | Fecha de publicación: | 12-oct-2020 | Editor: | American Chemical Society | Citación: | Organic Letters 22 (21) 8345-8348 (2020) | Resumen: | We have developed a new method for the stereoselective establishment of the N-acyl hemiaminal moiety in zampanolide-type structures that involves the reaction of (Z,E)-sorbamide (3) with BINAL-H and subsequent amide transfer froma putative aluminum carboximidoate complex to the aldehyde moiety of a dactylolide precursor, such as 2 or 5. The method has enabled the efficient synthesis of 13-desmethylene-(−)-zampanolide (4), which was found to be an equipotent cell growth inhibitor as the natural product (−)-zampanolide (1). | Descripción: | 4 p.-1 fig.-1 tab.-i graph. abst.-5 schem. | Versión del editor: | https://doi.org/10.1021/acs.orglett.0c02974 | URI: | http://hdl.handle.net/10261/228210 | DOI: | 10.1021/acs.orglett.0c02974 | ISSN: | 1523-7060 | E-ISSN: | 1523-7052 |
| Aparece en las colecciones: | (CIB) Artículos |
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| accesoRestringido.pdf | Restringido | 15,38 kB | Adobe PDF |  Visualizar/Abrir |
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