A concise total synthesis of the TMC-95A and TMC-95B proteasome inhibitors
| dc.contributor.author | Albrecht, Brian Keith, author | |
| dc.contributor.author | Williams, Robert M., advisor | |
| dc.date.accessioned | 2022-11-28T17:46:42Z | |
| dc.date.available | 2022-11-28T17:46:42Z | |
| dc.date.issued | 2004 | |
| dc.description.abstract | A 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. | |
| dc.format.medium | doctoral dissertations | |
| dc.identifier.uri | https://hdl.handle.net/10217/235846 | |
| dc.language | English | |
| dc.language.iso | eng | |
| dc.publisher | Colorado State University. Libraries | |
| dc.relation | Catalog record number (MMS ID): 991020102319703361 | |
| dc.relation | QP609.P78A537 2004 | |
| dc.relation.ispartof | 2000-2019 | |
| dc.rights | Copyright 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. | |
| dc.subject | Protease inhibitors | |
| dc.subject | Ubiquitin | |
| dc.title | A concise total synthesis of the TMC-95A and TMC-95B proteasome inhibitors | |
| dc.type | Text | |
| dcterms.rights.dpla | This Item is protected by copyright and/or related rights (https://rightsstatements.org/vocab/InC/1.0/). You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). | |
| thesis.degree.discipline | Chemistry | |
| thesis.degree.grantor | Colorado State University | |
| thesis.degree.level | Doctoral | |
| thesis.degree.name | Doctor of Philosophy (Ph.D.) |
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