Department of Chemistry and Biochemistry, University of Denver, Denver, Colorado 80208, USA.
J Org Chem. 2011 Mar 4;76(5):1319-32. doi: 10.1021/jo102221q. Epub 2011 Jan 26.
Chromones are introduced into a double-tandem [4(π)+2(π)]·[2(π)+2(π)]·[4(π)+2(π)]·[2(π)+2(π)] synthetic sequence, culminating in photoprotolytic oxametathesis, which leads to an expeditious growth of molecular complexity over a few experimentally simple steps. The overall reaction can potentially be utilized in diversity-oriented synthesis, as it allows for three or more diversity inputs furnishing novel unique polycyclic scaffolds decorated with a variety of functionalities and aromatic/heterocyclic pendants. The polycyclic alkenes, resulting from the oxametathesis step, were found to undergo efficient and clean photoinduced epoxidation when irradiated in the presence of molecular oxygen.
色烯被引入到一个双重串联的[4(π)+2(π)]·[2(π)+2(π)]·[4(π)+2(π)]·[2(π)+2(π)]合成序列中，最终通过光致解环氧化偶联反应，在几个实验上简单的步骤中快速增加分子的复杂性。该整体反应可能在多样性导向合成中得到应用，因为它允许三个或更多的多样性输入提供新颖独特的多环支架，这些支架用各种官能团和芳族/杂环侧链进行修饰。在存在分子氧的情况下，当用光照射时，来自环氧化偶联步骤的多环烯烃被发现能够有效地、干净地进行光诱导环氧化。
