A concise synthesis of the naphthalene portion of purpuromycin.

Andrew N Lowell, Michael W Fennie, Marisa C Kozlowski

Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.

The Journal of organic chemistry 2008 Mar 7

filter terms:

A concise synthesis of naphthalene compounds for incorporation into a synthetic sequence for the rubromycin family of natural products is presented. These highly substituted naphthalenes are generated in seven and nine steps, respectively, from 2,4,5-trimethoxybenzaldehyde. Three ring-forming methods were explored and the controlled oxygenation of different positions was investigated to yield differentially substituted/protected systems. Key steps to the final products include a Stobbe condensation to form the ring system and a novel series of regioselective oxidations to introduce the required oxygen functionality. These naphthalene products incorporate orthogonal protecting groups and are suitable for combination with a variety of coupling partners.

Citation

Andrew N Lowell, Michael W Fennie, Marisa C Kozlowski. A concise synthesis of the naphthalene portion of purpuromycin. The Journal of organic chemistry. 2008 Mar 7;73(5):1911-8