Levoglucosenone and Its Pseudoenantiomer <i>iso</i>-Levoglucosenone as Scaffolds for Drug Discovery and Development

Abstract

The bioderived platform molecule levoglucosenone (LGO, <b>1</b>) and its readily prepared pseudoenantiomer (<i>iso</i>-LGO, <b>2</b>) have each been subjected to α-iodination reactions with the product halides then being engaged in palladium-catalyzed Ullmann cross-coupling reactions with various bromonitropyridines. The corresponding α-pyridinylated derivatives such as <b>11</b> and <b>24</b>, respectively, are produced as a result. Biological screening of such products reveals that certain of them display potent and selective antimicrobial and/or cytotoxic properties. In contrast, the azaindoles obtained by reductive cyclization of compounds such as <b>11</b> and <b>12</b> are essentially inactive in these respects. Preliminary mode-of-action studies are reported.