Synthesis of Piericidins A1 and B1

Significance

Piericidin A1 is a nM inhibitor of NADH-ubiquinone reductase, a mitochondrial electron transport chain protein. The synthesis by Schnermann and Boger determined the absolute stereochemistry and is noteworthy for (1) the preparation of sulfonylimine E by homolytic rearrangement of oxime sulfinate B (see: C. Brown et al. J. Chem. Soc., Perkin Trans. 2 1978, 822-828) and (2) the expedient synthesis of functionalized pyridine G by an inverse electron demand Diels-Alder reaction.