Synthesis of the Core Structure of Sungeidine Natural Products

在该项目的过程中，打算采用一种合成路线来获取Sungeidine天然产物的核心。Sungeidines是由烯-二炔类微生物生物合成基因簇产生的一类次生代谢物。由于动力霉素类化合物的相关生物合成烯-二炔前体具有有趣的药理性质，其次级代谢产物也被认为具有新的生物活性。作为关键步骤，将开发一种新的(4+2)-环加成反应(Diels-Alder反应)，为此，原位生成且迄今未被开发的氧代吡咯离子将与活化的二烯反应。它们的原位生成将依赖于光或电化学方法，其中二氢吡咯-2-酮是前身。此外，还可以实现一种新的合成策略来获得(寡聚)取代的吡咯烷酮，这些取代的吡咯烷酮代表了广泛存在于各种化合物类中的常见杂环基序。一旦合成策略用于合成Sungeidine核心的可行性被证明，不同的起始原料的改变允许合成不同的sungeidine。

In the course of the project, a synthetic route to access the core of sungeidine natural products is intended. Sungeidines are a class of secondary metabolites generated by microbial biosynthetic gene clusters from ene-diynes. Because related biosynthetic ene-diyne precursors of the dynemicin-type possess interesting pharmacological properties, secondary metabolites of such are thought to potentially exhibit novel bioactive characteristics too.As key step, a novel (4+2)-cycloaddition (Diels-Alder reaction) will be developed, for which in-situ generated and to this date underexplored oxopyrrolium ions shall be reacted with activated dienes. Their in-situ generation will rely on photo- or electrochemical approaches, in which dihydropyrrol-2-ones serve as predecessors. In addition, a new synthetic strategy to access (oligo)substituted pyrrolidinones, which represent common heterocyclic motifs found in a large variety of compound classes, can be achieved.Once the synthetic strategy’s feasibility for the synthesis of the sungeidine core has been proven, alterations of the different starting materials allow the synthesis of different sungeidines.