Record number :
1890385
Title of article :
A synthetic approach to palmerolides via Negishi cross coupling. The challenge of the C15–C16 bond formation
Author/Authors :
Carrillo، نويسنده , , Jokin and Gَmez، نويسنده , , Alex and Costa، نويسنده , , Anna M. and Fernلndez، نويسنده , , Patricia and Isart، نويسنده , , Carles and Sidera، نويسنده , , Mireia and Vilarrasa، نويسنده , , Jaume، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2014
Pages :
5
From page :
4623
To page :
4627
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.
Keywords :
Melanoma-inhibiting macrolides , Palmerolides , Screening of phosphine ligands , Negishi cross-coupling reactions
Journal title :
Tetrahedron Letters
Serial Year :
2014
Link To Document :
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