1. A versatile, non-biomimetic route to the preussomerins: syntheses of (±)-preussomerins F,K and L
- Author
-
Richard J. K. Taylor, Michael E. Prime, Martin Stockley, Ernesto Quesada, Adrian C. Whitwood, and Jacques P. Ragot
- Subjects
Models, Molecular ,Tandem ,Stereochemistry ,Chemistry ,Organic Chemistry ,Molecular Conformation ,Regioselectivity ,Stereoisomerism ,Biochemistry ,Combinatorial chemistry ,Heterocyclic Compounds, 4 or More Rings ,Molecular conformation ,Epoxy Compounds ,Physical and Theoretical Chemistry - Abstract
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.
- Published
- 2004