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Organic & Biomolecular Chemistry

The international home of synthetic, physical and biomolecular organic chemistry.




Issue 18 of OBC


29 August 2008

The enantioselective Diels-Alder reaction is one of the most important reactions for the synthesis of complex molecules. It provides access to chiral six-membered carbocyclic compounds containing up to four stereogenic centers in a single step. In this issue's Perspective, Juan Shen and Choon-Hong Tan from the National University of Singapore describe several cases of chiral Brønsted-acid and Brønsted-base catalyzed Diels-Alder reactions, providing an overview of this rapidly growing field. 

Brønsted-acid and Brønsted-base catalyzed Diels-Alder reactions

This issue's cover was provided by Peter Wipf at the University of Pittsburgh and colleagues. In their paper they describe the computational design, synthesis and biological evaluation of quinone-based inhibitors for redox regulation of the dual-specificity phosphatase Cdc25B.

From a virtual chemical library of quinone-based inhibitors (white) of the dual specificity phosphatase Cdc25B (red, in background), LCAP search algorithms identified the electronically most suitable lead structure (CPK model, front view).

References

Juan Shen and Choon-Hong Tan, Org. Biomol. Chem., 2008, DOI:  10.1039/b809505c

Shahar Keinan, William D. Paquette, John J. Skoko, David N. Beratan, Weitao Yang, Sunita Shinde, Paul A. Johnston, John S. Lazo and Peter Wipf, Org. Biomol. Chem., 2008, DOI:  10.1039/b806712k


Organic & Biomolecular Chemistry Issue 18

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