Organic Letters 2013-02-01

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

Johannes Hoecker, Karl Gademann

Index: Org. Lett. 15(3) , 670-3, (2013)

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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.