title: Stereochemical Assignment of the Protein-Protein Interaction Inhibitor JBIR-22 by Total Synthesis.
abstract: Recent reports have highlighted the biological activity associated with a subfamily of the tetramic acid class of natural products. Despite the fact that members of this subfamily act as protein-protein interaction inhibitors that are of relevance to proteasome assembly, no synthetic work has been reported. This may be due to the fact that this subfamily contains an unnatural 4,4-disubstitued glutamic acid, the synthesis of which provides a key challenge. A highly stereoselective route to a masked form of this unnatural amino acid now enabled the synthesis of two of the possible diastereomers of JBIR-22 and allowed the assignment of its relative and absolute stereochemistry.
authors.forename: Alan R
authors.initials: AR
authors.lastname: Healy
authors.forename: Miho
authors.initials: M
authors.lastname: Izumikawa
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.forename: Kazuo
authors.initials: K
authors.lastname: Shin-Ya
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Westwood
keywords: Naturstoffe; Nichtnatürliche Aminosäuren; Stereochemie; Tetraminsäuren; Totalsynthese