| Title: | De Novo Asymmetric Synthesis and Biological Analysis of the Daumone Pheromones in Caenorhabditis elegans and in the Soybean Cyst Nematode Heterodera glycines |
| Author(s): | Guo H; La Clair JJ; Masler EP; O'Doherty G; Xing Y; |
| Address: | "School of Nuclear Technology and Chemistry & Life Science, Hubei University of Science and Technology, Xianning 437100, China. Xenobe Research Institute, P. O. Box 3052, San Diego, CA 92163-1052, USA. Nematology Laboratory, USDA-ARS-NEA, Beltsville MD 20705, USA. Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, USA. Department of Chemistry, William Paterson University, 300 Pompton Rd, Wayne, NJ 07470, USA" |
| DOI: | 10.1016/j.tet.2016.03.033 |
| ISSN/ISBN: | 0040-4020 (Print) 0040-4020 (Linking) |
| Abstract: | "The de novo asymmetric total syntheses of daumone 1, daumone 3 along with 5 new analogs are described. The key steps of our approach are: the diastereoselective palladium catalyzed glycosylation reaction; the Noyori reduction of 2-acetylfuran and an ynone, which introduce the absolute stereochemistry of the sugar and aglycon portion of daumone; and an Achmatowicz rearrangement, an epoxidation and a ring opening installing the remaining asymmetry of daumone. The synthetic daumones 1 and 3 as well as related analogs were evaluated for dauer activity in C. elegans and for effects on hatching of the related nematode H. glycines. This data provides additional structure activity relationships (SAR) that further inform the study of nematode signaling" |
| Keywords: | Pd-glycosylation dauer activity daumone pheromones de novo asymmetric synthesis hatching effect; |
| Notes: | "PubMed-not-MEDLINEGuo, Haibing La Clair, James J Masler, Edward P O'Doherty, George Xing, Yalan eng R01 GM090259/GM/NIGMS NIH HHS/ England 2016/05/05 Tetrahedron. 2016 May 5; 72(18):2280-2286. doi: 10.1016/j.tet.2016.03.033. Epub 2016 Mar 16" |
