Download PDF
Synfacts 2006(4): 0313-0313  
DOI: 10.1055/s-2006-932032
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Piericidins A1 and B1

Contributor(s): Philip Kocienski, Thomas Snaddon
M. J. Schnermann, D. L. Boger*
The Scripps Research Institute, La Jolla, USA
Further Information

Publication History

Publication Date:
24 March 2006 (online)

    Permissions and Reprints

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.