Albrecht, Brian Keith, authorWilliams, Robert M., advisor2022-11-282022-11-282004https://hdl.handle.net/10217/235846A concise total synthesis of the TMC-95A/B proteasome inhibitors is presented. The synthesis features the use of an L-serine derived E-selective modified Julia olefination reaction that ultimately controls the stereochemical outcome of the highly oxidized tryptophan fragment. A diastereoselective dihydroxylation, a Suzuki coupling, macrocyclization and cis-propenyl amide formation were also employed. In the process of the total synthesis, a suitable intermediate was converted to a late stage intermediate in the Danishefsky total synthesis, effectively completing a formal synthesis. The limited use of protecting groups allowed for an efficient route that is amenable to the preparation of a variety of analogs due to its convergency.doctoral 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.Protease inhibitorsUbiquitinText