The stereoselective synthesis of a challenging macrocyclic polyene scaffold, containing a sensitive vinyl ether motif, has been accomplished using O,C-dilithiation/selective C-alkylation, Pd-catalysed etherification and Wittig reactions as key steps. An end-game macrocyclisation strategy employed a regio- and stereoselective Stille cross-coupling using Pd(Br)(N-Succ)(AsPh3)2 (AsCat) as the precatalyst.
T. O. Ronson, M. H. H. Voelkel, R. J. K. Taylor and I. J. S. Fairlamb, Chem. Commun., 2015, 51, 8034 DOI: 10.1039/C5CC02091C
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