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http://hdl.handle.net/2445/63190
Title: | A synthetic approach to palmerolides via Negishi cross coupling. The challenge of the C15-C16 bond formation |
Author: | Carrillo Arregui, Jokin Gómez, Álex Costa i Arnau, Anna M. Fernández, Patricia Isart Garriga, Carles Sidera Portela, Mireia Vilarrasa i Llorens, Jaume |
Keywords: | Melanoma Antibiòtics Quimioinformàtica Química organometàl·lica Melanoma Antibiotics Cheminformatics Organometallic chemistry |
Issue Date: | 21-Jun-2014 |
Publisher: | Elsevier Ltd |
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. |
Note: | Versió postprint del document publicat a: http://dx.doi.org/10.1016/j.tetlet.2014.06.066 |
It is part of: | Tetrahedron Letters, 2014, vol. 55, num. 33, p. 4623-4627 |
URI: | http://hdl.handle.net/2445/63190 |
Related resource: | http://dx.doi.org/10.1016/j.tetlet.2014.06.066 |
ISSN: | 0040-4039 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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