Lowell Andrew N, Fennie Michael W, Kozlowski Marisa C
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
J Org Chem. 2008 Mar 7;73(5):1911-8. doi: 10.1021/jo7024114. Epub 2008 Feb 8.
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.
本文介绍了一种用于萘化合物的简洁合成方法，该方法可将其纳入天然产物红霉霉素家族的合成序列中。这些高度取代的萘分别由2,4,5-三甲氧基苯甲醛经过七步和九步反应生成。研究了三种成环方法，并对不同位置的可控氧化进行了研究，以得到不同取代/保护的体系。最终产物的关键步骤包括形成环系的斯托贝缩合反应和一系列引入所需氧官能团的新型区域选择性氧化反应。这些萘产物含有正交保护基，适用于与多种偶联试剂结合。
