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Título: | Highly Stereoselective Total Synthesis of (+)-9-epi-Dictyostatin and (–)-12,13-bis-epi-Dictyostatin Eur. J |
Autor: | Zanato, Chiara; Pignataro, Luca; Ambrosi, Andrea; Hao, Zhongyan; Trigili, Chiara CSIC; Díaz, José Fernando CSIC ORCID ; Barasoain, Isabel CSIC ; Gennari, Cesare | Palabras clave: | Medicinal chemistry Natural products Total synthesis Asymmetric synthesis Antitumor agents Macrocycles |
Fecha de publicación: | may-2011 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry(14):2643-2661(2011) | Resumen: | The total syntheses of (+)-9-epi-dictyostatin (1a) and (–)-12,13-bis-epi-dictyostatin (1b), diastereomers of the antimitotic marine sponge-derived macrolide (–)-dictyostatin (1), were achieved by creating 11 stereogenic centers and 4stereogenic double bonds with a high level of stereocontrol. The yield for the 29-step longest linear sequence from Roche ester was 1.53 and 1.52 %, respectively. The final key steps to these unnatural products were the addition of vinylzincates C10-C26 to aldehyde C1–C9 (leading surprisingly to complete stereoselectivity for the 9R-configuration in 28a and for the 9S-configuration in 12,13-bis-epimeric 28b), followed by Yamaguchi macrolactonization and global deprotection. (–)-12,13-Bis-epi-dictyostatin (1b) displayed a dramatic decrease of cytotoxicity and of the affinity toward the paclitaxel binding site of microtubules | Descripción: | 19 páginas, 9 esquemas, 2 tablas -- PAGS nros. 2643-2661 | Versión del editor: | http:dx.doi.org/10.1002/ejoc.201100244 | URI: | http://hdl.handle.net/10261/51678 | DOI: | 10.1002/ejoc.201100244 | ISSN: | 0022-3263 | E-ISSN: | 1520-6904 |
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