title: Synthesis and Antibacterial Activity of Four Stereoisomers of the Spider-Pathogenic Fungus Metabolite Torrubiellone D.
abstract: Four stereoisomers of the spider-pathogenic fungus metabolite torrubiellone D were synthesized for the first time in 10% overall yield starting from L-tyrosine or D-tyrosine. The 3-decatrienoyl side chain was assembled and attached via (E)-selective HWE and Wittig olefinations. Their antibiotic activities against drug-susceptible Escherichia coli strains differed considerably.
authors.affiliation: Organic Chemistry Laboratory, University Bayreuth , Universitaetsstrasse 30, 95440 Bayreuth, Germany.
authors.forename: Sebastian
authors.initials: S
authors.lastname: Bruckner
authors.affiliation: Helmholtz Centre for Infection Research, Inhoffenstrasse 7, 38124 Braunschweig, Germany.
authors.forename: Ursula
authors.initials: U
authors.lastname: Bilitewski
authors.affiliation: Organic Chemistry Laboratory, University Bayreuth , Universitaetsstrasse 30, 95440 Bayreuth, Germany.
authors.forename: Rainer
authors.initials: R
authors.lastname: Schobert
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D016984:Enterococcus faecium / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D006999:Hypocreales / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000737:chemistry; D013112:Spiders / Q000382:microbiology*; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D014443:Tyrosine / Q000737:chemistry
chemical_list: D000470:Alkaloids; D000900:Anti-Bacterial Agents; D011760:Pyrrolidinones; C000609065:torrubiellone D; D014443:Tyrosine; C009435:tetramic acid