title: A Synthetic Route to β-Hydroxytyrosine-Derived Tetramic Acids: Total Synthesis of the Fungal Metabolite F-14329.
abstract: 3-Acyltetramic acids derived from β-hydroxytyrosine are synthetically challenging. The first route to this structural motif, based upon a condensation between a Meldrum's acid conjugate bearing the acyl side chain, and a β-hydroxytyrosinate, N-protected by an ortho-nitrobenzyl group is presented. This group enables the Dieckmann cyclization of the resulting N-(β-ketoacyl)amino ester, after which it can be removed photolytically without compromising the delicate 3'-hydroxy group. This strategy was applied to the first total synthesis of the fungal metabolite F-14329 (1).
authors.affiliation: Organic Chemistry Laboratory, University Bayreuth, Universitaetsstr. 30, 95447, Bayreuth, Germany.
authors.forename: Sebastian
authors.initials: S
authors.lastname: Bruckner
authors.affiliation: Organic Chemistry Laboratory, University Bayreuth, Universitaetsstr. 30, 95447, Bayreuth, Germany.
authors.forename: Robert G
authors.initials: RG
authors.lastname: Haase
authors.affiliation: Organic Chemistry Laboratory, University Bayreuth, Universitaetsstr. 30, 95447, Bayreuth, Germany.
authors.forename: Rainer
authors.identifier: http://orcid.org/0000-0002-8413-4342
authors.initials: R
authors.lastname: Schobert
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D005658:Fungi / Q000378:metabolism*; D010143:Paecilomyces / Q000378:metabolism; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013720:Tenuazonic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001688:Biological Products; D011760:Pyrrolidinones; C009435:tetramic acid; D013720:Tenuazonic Acid; C000601007:F-14329
keywords: F-14329; chaunolidines; natural products; tetramic acids; total synthesis