Klas, Kimberly R., authorWilliams, Robert M., advisorShi, Yian, committee memberChen, Eugene, committee memberCrick, Dean, committee member2019-09-102019-09-102019https://hdl.handle.net/10217/197296Various fungi of the genera Aspergillus, Penicillium and Malbranchea produce prenylated indole alkaloids that possess a bicyclo[2.2.2]diazaoctane ring system and a variety of biological activities such as insecticidal, cytotoxic, anthelmintic, and antibacterial properties. After the discovery of distinct enantiomers of the natural alkaloids Stephacidin A, Notoamide B and their corresponding diastereomers, from Aspergillus protuberus MF297-2, Aspergillus amoenus NRRL 35660 and Aspergillus taichungensis, the structurally diverse metabolites became of particular biosynthetic interest. The bicyclo[2.2.2]diazaoctane core of the divergent natural metabolites may be enzymatically derived via a putative intramolecular hetero-Diels-Alder cycloaddition. We completed the total synthesis of ZwtP and MeZwtP, unveiling the role of a newly discovered Diels-Alderase. We are also undergoing further synthetic efforts to access other novel natural products, as well as further understand additional unprecedented transformations in nature.born digitaldoctoral dissertationsengCopyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright.citrinalinnatural productsZwtPDiels-Alderasebrevianamideprenylated indole alkaloidsText