Diversity-oriented synthetic strategies toward N-heterocyclic and carbocyclic frameworks

Heterocycles;Cyclopropanes;Cyclobutanes;Polycarbocycles;Natural products;Dehydrative Nazarov cyclization

Martin, Maria Cynthia ; Finn, M. G. Chemistry and Biochemistry France, Stefan Collard, David Kelly, Wendy L. Bommarius, Andy ; Finn, M. G.

University:Georgia Institute of Technology

Department:Chemistry and Biochemistry

关键词: Heterocycles;    Cyclopropanes;    Cyclobutanes;    Polycarbocycles;    Natural products;    Dehydrative Nazarov cyclization;   

Others  :  https://smartech.gatech.edu/bitstream/1853/58727/1/MARTIN-DISSERTATION-2017.pdf

美国|英语

来源: SMARTech Repository

【 摘 要 】

N-Heterocyclic and polycyclic molecular scaffolds are valuable structural motifs present in many biologically active and pharmaceutically-relevant compounds, and also in the field of material science. Much effort has been focused on the development of efficient methods for the formation of these significant scaffolds for the synthesis of natural product targets. In the following thesis, diverse protocols have been designed to access these heterocyclic and carbocyclic targets: (1) the use of strained polarized ring systems in the presence of amine nucleophiles to access small N-heterocyclic molecules, (2) the design of a formal [5+2] cycloaddition approach towards seven-membered ring fused indoles, and (3) the dehydrative, Nazarov-type cyclization via calcium catalysis to access directly a wide array of cyclopenta[b]thiophenes and indenes. All these catalytic transformations are amenable to various functional groups, thus demonstrating their versatility and scope.