Chemistry

Diverse Scaffolds

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Science  02 Jan 2009:
Vol. 323, Issue 5910, pp. 17
DOI: 10.1126/science.323.5910.17a

Chemical libraries are widely used in bioactivity studies and drug discovery, yet many such libraries cover only a limited range of chemical shapes, or molecular scaffolds. Morton et al. have now achieved a library of over 80 different scaffolds by exploiting the power of ring-closing metathesis, a process involving scission and redistribution of carbon-carbon double bonds that leads to the formation of ring systems. Using two types of building blocks and fluorous-tagged linkers, the authors prepared cyclic products in four or five steps using combinations of just six reaction types. The compounds prepared contained numerous structural features such as isolated, fused, and spirocyclic ring systems; intramolecular hydrogen bonding; unsaturation; and dense substitution that were reminiscent of natural products. Many of the scaffolds had not been previously synthesized. — JFU

Angew. Chem. Int. Ed. 10.1002/anie.200804486 (2008).

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