Valiulin Roman A, Kutateladze Andrei G
Department of Chemistry and Biochemistry, University of Denver, Colorado, USA.
Tetrahedron Lett. 2010 Jul 21;51(29):3803-3806. doi: 10.1016/j.tetlet.2010.05.078.
Diels-Alder adducts of chromones are shown to undergo an intramolecular [2(pi)+2(pi)] alkene-arene photocyclization, leading to a versatile polycyclic diene, which is capable of dimerization or can be introduced into a high yielding photoprotolytic oxametathetic sequence. This allows for an expeditious growth of molecular complexity over a few experimentally simple steps with stereochemistry being defined and locked at the very first Diels-Alder step. 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, which can readily be decorated with a variety of functionalities and aromatic/heterocyclic pendants.
已表明色酮的狄尔斯-阿尔德加合物会发生分子内[2(π)+2(π)]烯烃-芳烃光环化反应，生成一种通用的多环二烯，该多环二烯能够二聚，或者可引入高产率的光解质子转移氧杂复分解序列中。这使得能够通过几个实验操作简单的步骤迅速增加分子复杂性，立体化学在第一个狄尔斯-阿尔德步骤就已确定并锁定。由于该反应允许三个或更多的多样性输入，从而提供新颖独特的多环骨架，这些骨架可容易地用各种官能团以及芳香族/杂环侧基进行修饰，因此整个反应有可能用于多样性导向合成。
