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2014-06-21

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/63190

A synthetic approach to palmerolides via Negishi cross coupling. The challenge of the C15-C16 bond formation

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http://dx.doi.org/10.1016/j.tetlet.2014.06.066

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.

Subject

Melanoma, Antibiòtics, Quimioinformàtica, Química organometàl·lica

Subject (English)

Melanoma, Antibiotics, Cheminformatics, Organometallic chemistry

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Articles publicats en revistes (Química Inorgànica i Orgànica)

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CARRILLO ARREGUI, Jokin, et al. A synthetic approach to palmerolides via Negishi cross coupling. The challenge of the C15-C16 bond formation. Tetrahedron Letters. 2014. Vol. 55, num. 33, pags. 4623-4627. ISSN 0040-4039. [consulted: 14 of August of 2026]. Available at: https://hdl.handle.net/2445/63190

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