| Title: | Identification of a Grain Beetle Macrolide Pheromone and Its Synthesis by Ring-Closing Metathesis Using a Terminal Alkyne |
| Author(s): | Hotling S; Bittner C; Tamm M; Dahn S; Collatz J; Steidle JL; Schulz S; |
| Address: | "Institut fur Organische Chemie, Technische Universitat Braunschweig , Hagenring 30, 38106 Braunschweig, Germany. Institut fur Anorganische und Analytische Chemie, Technische Universitat Braunschweig , Hagenring 30, 38106 Braunschweig, Germany. Fachgebiet Tierokologie, Institut fur Zoologie, Universitat Hohenheim , 70593 Stuttgart, Germany" |
| DOI: | 10.1021/acs.orglett.5b02461 |
| ISSN/ISBN: | 1523-7052 (Electronic) 1523-7052 (Linking) |
| 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 [MesCMoOC(CF3)2Me3] (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 omega-4 position" |
| Keywords: | Alkynes/*chemistry Animals Anti-Bacterial Agents Coleoptera/*chemistry Edible Grain/parasitology Macrolides/*chemistry Molecular Structure Pheromones/*chemistry Protein Synthesis Inhibitors Stereoisomerism; |
| Notes: | "MedlineHotling, Susann Bittner, Celine Tamm, Matthias Dahn, Sonja Collatz, Jana Steidle, Johannes L M Schulz, Stefan eng 2015/09/26 Org Lett. 2015 Oct 16; 17(20):5004-7. doi: 10.1021/acs.orglett.5b02461. Epub 2015 Sep 25" |
