Volume 85 Issue 35 | p. 33 | Concentrates
Issue Date: August 27, 2007

Tetracycline synthesis improves

Department: Science & Technology
News Channels: Nano SCENE, Environmental SCENE
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In 2005, Andrew G. Myers and colleagues at Harvard University reported an enantioselective semisynthetic route to tetracyclines that yielded an unprecedented series of structurally diverse analogs of this broad-spectrum class of antibiotics. In an ongoing effort to develop a fully synthetic route to tetracyclines, Myers and graduate student Jason D. Brubaker now report a completely different pathway to a key precursor in the synthesis (Org. Lett., DOI: 10.1021/ol071377d). The precursor (shown) contains the A and B rings of the four-ring tetracycline molecule. Important steps in the new route, which proceeds in nine steps with 21% overall yield on a multigram scale, include enantioselective addition of divinylzinc to a heterocyclic starting material and an endo-selective intramolecular Diels-Alder cycloaddition. "We believe that this innovation will fuel the discovery of large numbers of new candidate antibiotics and may provide the basis for novel tetracyclines to be synthesized on a scale sufficient for their clinical development," they write.

 
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ISSN 0009-2347
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