Synthesis of a simplified analogue of eleutherobin via a Claisen rearrangement and ring closing metathesis strategy.
The enantioselective synthesis of a simplified eleutherobin analogue by ring closing metathesis (RCM) of the 2,9-divinyl-substituted tetrahydro-oxonin is described; the analogue and an advanced intermediate revealed microtubule stabilising properties in the micromolar range.
Chiang
Gary C H
GC
Department of Chemistry, University of Cambridge, UK.
Bond
Andrew D
AD
Ayscough
Andrew
A
Pain
Gilles
G
Ducki
Sylvie
S
Holmes
Andrew B
AB
D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure
D004224:Diterpenes; D004852:Epoxy Compounds; C109551:eleutherobin