title: Enantioselective total syntheses and absolute configuration of JBIR-02 and Mer-A2026B.
abstract: The first total syntheses of the piericidin related natural products Mer-A2026B and JBIR-02 are reported. Key features of the synthetic approach involve an Ir-catalyzed one-pot C-H activation/oxidation procedure for the preparation of the hydroxypyridine, a vinylogous Mukaiyama aldol reaction, and a final Negishi cross-coupling of an advanced pyridine derivative with an allylic side chain precursor. In addition, the absolute configuration of Mer-A2026B (9R,10R) and JBIR-02 (9R,10R) was established.
authors: Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland.
authors: Johannes
authors: J
authors: Hoecker
authors: Karl
authors: K
authors: Gademann
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C524347:JBIR-02 compound; C092866:Mer A2026B; D011725:Pyridines; D011728:Pyridones; C100213:piericidin A