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Issue 38, 2015
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Macrocyclic polyenynes: a stereoselective route to vinyl-ether-containing skipped diene systems

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Abstract

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.

Graphical abstract: Macrocyclic polyenynes: a stereoselective route to vinyl-ether-containing skipped diene systems

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Publication details

The article was received on 11 Mar 2015, accepted on 09 Apr 2015 and first published on 20 Apr 2015


Article type: Communication
DOI: 10.1039/C5CC02091C
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Chem. Commun., 2015,51, 8034-8036

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    Macrocyclic polyenynes: a stereoselective route to vinyl-ether-containing skipped diene systems

    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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