A versatile, non-biomimetic route to the preussomerins: syntheses of (+/-)-preussomerins F, K and L.
The first total syntheses of the title fungal metabolites preussomerins F, K and L are described and their structures confirmed thereby. The syntheses were achieved following a versatile, unified, non-biomimetic approach, which is easily extendable to prepare other known and novel members of this family. Key steps include the functionalisation of a 2-arylacetal anion, tandem one-pot Friedel-Crafts cyclisation-deprotection, regioselective substrate-directable hydrogenation and reductive-opening of epoxides.
Department of Chemistry, University of York, Heslington, York, UKYO10 5DD.
Ernesto
E
Quesada
Martin
M
Stockley
Jacques P
JP
Ragot
Michael E
ME
Prime
Adrian C
AC
Whitwood
Richard J K
RJ
Taylor
D004852:Epoxy Compounds / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D004852:Epoxy Compounds; D006576:Heterocyclic Compounds, 4 or More Rings; C501550:preussomerin F; C501551:preussomerin K; C501549:preussomerin L