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

TY - JOUR

T1 - Macrocyclic polyenynes

T2 - A stereoselective route to vinyl-ether-containing skipped diene systems

AU - Ronson, Thomas O.

AU - Voelkel, Martin H H

AU - Taylor, Richard J K

AU - Fairlamb, Ian J S

PY - 2015/5/11

Y1 - 2015/5/11

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84928963033&partnerID=8YFLogxK

U2 - 10.1039/c5cc02091c

DO - 10.1039/c5cc02091c

M3 - Article

C2 - 25891970

SN - 1359-7345

VL - 51

SP - 8034

EP - 8036

JO - Chemical Communications

JF - Chemical Communications

IS - 38

ER -