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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
Química organometàl·lica
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:
It is part of: Tetrahedron Letters, 2014, vol. 55, num. 33, p. 4623-4627
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ISSN: 0040-4039
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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