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Enantioselective total syntheses and absolute configuration of JBIR-02 and Mer-A2026B.
Journal article

Enantioselective total syntheses and absolute configuration of JBIR-02 and Mer-A2026B.

  • Hoecker J Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland.
  • Gademann K
  • 2013-01-22
Published in:
  • Organic letters. - 2013
Catalysis
Molecular Structure
Oxidation-Reduction
Pyridines
Pyridones
Stereoisomerism
English 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.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://folia.unifr.ch/global/documents/261024
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