Bioactive secondary metabolites are often excellent lead compounds for the development of therapeutic agents. Between 2000-2010 it is estimated that about 50% of all small molecule new chemical entities approved for therapeutics were inspired by natural products. Dimeric chromanones and tetrahydroxanthones possess particularly attractive antibacterial, antiviral, and anticancer properties. Unfortunately, the advancement of many chromanone and tetrahydroxanthone natural products into medicinal agents is inhibited because reliable methods to synthesize their rather complex structures are either underdeveloped or altogether missing. The discovery of methods for the stereoselective construction of these bioactive heterocycles would have an immense impact on the synthesis of chromanone-containing complex targets and should facilitate their associated drug development. We have recently discovered that silanediols can operate as unique catalytic tools for the enantioselective preparation of biologically relevant chromanones. Insights relevant to the development of silanediols as enantioselective anion-binding catalysts for chromanone construction, including plausible modes of actions, will be presented.

Silanediols in enantioselective catalysis and complex molecule synthesis

2019 Spring National Meeting

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