title: 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.
authors.affiliation: Department of Chemistry, University of York, York, YO10 5DD, UK. richard.taylor@york.ac.uk ian.fairlamb@york.ac.uk.
authors.forename: Thomas O
authors.initials: TO
authors.lastname: Ronson
authors.forename: Martin H H
authors.initials: MH
authors.lastname: Voelkel
authors.forename: Richard J K
authors.initials: RJ
authors.lastname: Taylor
authors.forename: Ian J S
authors.initials: IJ
authors.lastname: Fairlamb
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D011083:Polycyclic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D000480:Alkynes; D004987:Ethers; D047028:Macrocyclic Compounds; D009942:Organometallic Compounds; D011083:Polycyclic Compounds; D014753:Vinyl Compounds