Issue Date: January 2, 2006
Natural-product-like compounds via a one-pot reaction
A new class of rapid, one-pot, multicomponent reactions may prove useful for creating libraries of complex natural-product-like compounds (J. Am. Chem. Soc. 2006, 128, 66). In the reaction (shown), a lithiated nucleophile (Nu-Li+) reacts with an epoxide substrate bearing a trialkylsilyl group and an anion-stabilizing group (ASG). The nucleophile opens the epoxide ring and alkylates the substrate, forming an oxyanion. A solvent-promoted transfer of the silyl group from carbon to oxygen causes the anionic center to move to the carbon atom adjacent to the ASG (this step not shown). Finally, the resulting carbanion is alkylated by an electrophilic reagent (E+). Chemistry professor Amos B. Smith III and postdoc Ming Xian at the University of Pennsylvania developed the synthetic technique, which they call anion relay chemistry, or ARC. Herbert Waldmann of Max Planck Institute of Molecular Physiology, Dortmund, Germany, says he views the technique "as an important step in the direction of synthesizing natural-product-derived compound collections in their full molecular complexity."
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