Título:
|
A synthetic approach to palmerolides via Negishi cross coupling. The challenge of the C15-C16 bond formation
|
Autor/a:
|
Carrillo Arregui, Jokin; Gómez, Álex; Costa i Arnau, Anna M.; Fernández, Patricia; Isart Garriga, Carles; Sidera Portela, Mireia; Vilarrasa i Llorens, Jaume
|
Otros autores:
|
Universitat de Barcelona |
Abstract:
|
The esterification of fragment C1-C8 (2) with fragment C16-C23 (3) to give iodo derivative 4, followed by a Pd-catalysed coupling with a C9-C15 fragment (7 or 8), may provide a common precursor of most palmerolides. Ligands and reaction conditions were exhaustively examined to perform the C15-C16 bond formation via Negishi reaction. With simple models, pre-activated Pd-Xantphos and Pd-DPEphos complexes were the most efficient catalysts at RT. Zincation of the C9-C15 fragment (8) and cross coupling with 4 required 3 equiv of t-BuLi, 10 mol % of Pd-Xantphos and 60 °C. |
Materia(s):
|
-Melanoma -Antibiòtics -Quimioinformàtica -Química organometàl·lica -Melanoma -Antibiotics -Cheminformatics -Organometallic chemistry |
Derechos:
|
(c) Elsevier Ltd, 2014
|
Tipo de documento:
|
Artículo Artículo - Versión aceptada |
Editor:
|
Elsevier Ltd
|
Compartir:
|
|