| Title: | Short stereoselective synthesis of the Phytophthora universal mating hormone alpha1 using lithiation/borylation reactions |
| Author(s): | Pulis AP; Fackler P; Aggarwal VK; |
| Address: | "School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS (UK) http://www.bris.ac.uk/chemistry/research/organic/aggarwal-group" |
| ISSN/ISBN: | 1521-3773 (Electronic) 1433-7851 (Linking) |
| Abstract: | "The universal mating hormone alpha 1 of the virulent plant pathogen Phytophthora has been synthesized in 12 steps and 28 % overall yield. Key C?╖?C bond-forming steps involved the use of two lithiation/borylation reactions to couple together enantioenriched building blocks, one of which also set up the stereochemistry of the tertiary alcohol at C11. Detailed analysis showed that the diastereomeric purity of the target molecule was >91 %, the highest obtained to date" |
| Keywords: | Boron/*chemistry Lithium/*chemistry Mating Factor Molecular Structure Peptides/*chemical synthesis Pheromones/*chemical synthesis *Phytophthora Stereoisomerism asymmetric synthesis boron lithium natural products total synthesis; |
| Notes: | "MedlinePulis, Alexander P Fackler, Philipp Aggarwal, Varinder K eng Research Support, Non-U.S. Gov't Germany 2014/03/19 Angew Chem Int Ed Engl. 2014 Apr 22; 53(17):4382-5. doi: 10.1002/anie.201400714. Epub 2014 Mar 14" |
