title: Identification of a Grain Beetle Macrolide Pheromone and Its Synthesis by Ring-Closing Metathesis Using a Terminal Alkyne.
abstract: A major C18-macrolide was found during analysis of the frass of the storage beetle Oryzaephilus surinamensis to be (9Z,12Z,15R)-octadeca-9,12-dien-15-olide (10, cucujolide XI). The synthesis used ring-closing alkyne metathesis as a key step. The highly active 2,4,6-trimethylbenzylidyne molybdenum complex [MesCMo{OC(CF3)2Me}3] (12) allowed the use of a terminal alkyne and afforded the product in excellent yield. Bioassays proved the activity of the R-enantiomer 10 in the aggregation of the beetle. Cucujolide XI is the first macrolide pheromone oxidized at the ω-4 position.
authors.affiliation: Institut für Organische Chemie, Technische Universität Braunschweig , Hagenring 30, 38106 Braunschweig, Germany.
authors.forename: Susann
authors.initials: S
authors.lastname: Hötling
authors.affiliation: Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig , Hagenring 30, 38106 Braunschweig, Germany.
authors.forename: Celine
authors.initials: C
authors.lastname: Bittner
authors.affiliation: Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig , Hagenring 30, 38106 Braunschweig, Germany.
authors.forename: Matthias
authors.initials: M
authors.lastname: Tamm
authors.affiliation: Fachgebiet Tierökologie, Institut für Zoologie, Universität Hohenheim , 70593 Stuttgart, Germany.
authors.forename: Sonja
authors.initials: S
authors.lastname: Dähn
authors.affiliation: Fachgebiet Tierökologie, Institut für Zoologie, Universität Hohenheim , 70593 Stuttgart, Germany.
authors.forename: Jana
authors.initials: J
authors.lastname: Collatz
authors.affiliation: Fachgebiet Tierökologie, Institut für Zoologie, Universität Hohenheim , 70593 Stuttgart, Germany.
authors.forename: Johannes L M
authors.initials: JL
authors.lastname: Steidle
authors.affiliation: Institut für Organische Chemie, Technische Universität Braunschweig , Hagenring 30, 38106 Braunschweig, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Schulz
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000818:Animals; D000900:Anti-Bacterial Agents; D001517:Coleoptera / Q000737:chemistry*; D002523:Edible Grain / Q000469:parasitology; D018942:Macrolides / Q000737:chemistry*; D015394:Molecular Structure; D010675:Pheromones / Q000737:chemistry*; D011500:Protein Synthesis Inhibitors; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000900:Anti-Bacterial Agents; D018942:Macrolides; D010675:Pheromones; D011500:Protein Synthesis Inhibitors