Issue 38, 2015

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

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

Supplementary files

Article information

Article type
Communication
Submitted
11 Mar 2015
Accepted
09 Apr 2015
First published
20 Apr 2015

Chem. Commun., 2015,51, 8034-8036

Author version available

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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