Editor's Summary
22 March 2007
Spurning protection
Total synthesis, which involves the construction of complex organic molecules from simpler starting materials, has made remarkable progress in the past fifty years. Despite this, the demand for new synthetic routes capable of generating large natural products for further biological studies remains high. A team of chemists has now identified the abandonment of the routine use of 'protecting' groups in synthesis as a way of satisfying this demand. Protecting groups are often used to mask reactive parts of a molecule while chemical transformations take place elsewhere in that molecule. The potential of the 'unprotected' approach was demonstrated by the synthesis of several members of a large class of marine alkaloids without using a single protecting group. The procedure yields significant quantities of molecules that previously required 20 or more distinct chemical operations in 10 steps or fewer.
News and Views: Organic chemistry: Synthesis undressed
Fragile chemical groups can be shielded from harsh reaction conditions by temporary protection. This approach is conventional wisdom for organic synthesis, but is it always the best solution?
John A. Porco, Jr
doi:10.1038/446383a
Article: Total synthesis of marine natural products without using protecting groups
Phil S. Baran, Thomas J. Maimone & Jeremy M. Richter
doi:10.1038/nature05569
Abstract | Full Text | PDF (463K) | Supplementary information