新型不对称aza-Nazarov电环化反应研究及在青藤碱等若干生物碱全合成中的应用

众所周知，有机合成新反应、新方法的发展对于促进有机化学自身及相关交叉领域，如合成药物化学、生物有机化学及材料科学等学科的发展都具有重要的科学意义。随着人们对于合成结构复杂的功能有机分子效率越来越高的期待，发展具有高的化学和立体选择性、通用性强的碳-碳成键或构环新反应和方法显得尤为重要。本项目拟在前期工作基础上进一步深入、系统地开展新型aza-Nazarov 环化反应的研究，尤其是不对称催化方法的探索和开发，并进而将这一新反应和方法作为关键步骤应用于若干含有特征的吡咯并氢化环戊烷单元结构类型的天然生物碱，包括青藤碱(-)-Sinoracutine、山橙属生物碱(+)-Meloscine及海洋生物碱(-)-Nakadomarin A 的全合成中。这些研究内容和实验结果将有益于丰富构建多官能团取代的五元碳环结构的新合成方法，并促进相应天然产物的高效化学合成和应用。

As we all know, the development of novel synthetic methodologies has important scientific significance for organic chemistry and interrelated fields, such as pharmaceutical chemistry, bioorganic chemistry and material science. In order to meet the increasing demands on the efficiency in the synthesis of complex organic molecules, it is particularly important to develop new reactions and methods for carbon-carbon bond or ring formation with high chemio- and stereoselectivity. Based on our preliminary work, the aza-Nazarov cyclization reaction will be explored deeply and systematically in this project, especially the asymmetric catalytic aza-Nazarov cyclization. Furthermore, the method will be applied in total synthesis of several alkaloids containing octahydrocyclopenta[b]pyrrole units, including (-)-Sinoracutine, (+)-Meloscine and (-)-Nakadomarin A. These studies will facilitate the synthesis of functionalized five membered carbon ring structure and corresponding natural products.