Aldrich Leslie N, Berry Cynthia B, Bates Brittney S, Konkol Leah C, So Miranda, Lindsley Craig W
Department of Chemistry, Vanderbilt University, Nashville, TN 37232-6600 (USA).
Departments of Pharmacology & Chemistry, Vanderbilt Center for Neuroscience Drug Discovery, 12415D MRBIV, Vanderbilt University Medical Center.
European J Org Chem. 2013 Jul 1;2013(20). doi: 10.1002/ejoc.201300643.
Herein, we describe the enantioselective construction of the 12-membered macrocyclic pyrrole core of marineosin A in 5.1% overall yield from ()-propylene oxide. The route features a key Stetter reaction to install a 1,4-diketone, which is then subjected to Paal-Knorr pyrrole synthesis and ring closing metathesis (RCM) to afford macrocycle A divergence point in the synthetic scheme also enabled access to a highly functionalized spiroaminal model system via an acid-mediated hydroxyketoamide cyclization strategy.
在此，我们描述了从（）-环氧丙烷以5.1%的总收率对海洋菌素A的12元大环吡咯核心进行对映选择性构建。该路线的特点是通过关键的施泰特反应引入一个1,4-二酮，然后进行帕尔-克诺尔吡咯合成和闭环复分解反应（RCM）以得到大环。合成方案中的一个分歧点还通过酸介导的羟基酮酰胺环化策略实现了对一个高度官能化的螺胺模型体系的构建。
