Asymmetric total syntheses of (+)- and (-)-spirotryprostatins A and B
| dc.contributor.author | Sebahar, Paul Richard, author | |
| dc.contributor.author | Williams, Robert M., advisor | |
| dc.date.accessioned | 2022-11-28T17:46:51Z | |
| dc.date.available | 2022-11-28T17:46:51Z | |
| dc.date.issued | 2003 | |
| dc.description.abstract | The first published total synthesis of (+)- and (-)-spirotryprostatin B is presented. The synthesis features an asymmetric azomethine ylide [1,3]-dipolar cycloaddition reaction. Additionally, a Barton-modified Hunsdiecker reaction was demonstrated as means of affecting an oxidative decarboxylation. Intermediates along the synthesis were studied for their biological activity as G2/M phase cell cycle inhibitors and microtubule assembly inhibitors. The asymmetric azomethine ylide [1,3]-dipolar cycloaddition was also studied in greater detail. Varying the aldehyde component of the reaction resulted in the formation three different cycloadducts. Theoretical calculations for the reaction were compared with observed results. Attempts to synthesize (-)-spirotryprostatin A are also presented. Two different strategies based on the synthesis of (+)- and (-)-spirotryprostatin B were explored. | |
| dc.format.medium | doctoral dissertations | |
| dc.identifier.uri | https://hdl.handle.net/10217/235864 | |
| dc.language | English | |
| dc.language.iso | eng | |
| dc.publisher | Colorado State University. Libraries | |
| dc.relation | Catalog record number (MMS ID): 991018481209703361 | |
| dc.relation | QD262.S434 2003 | |
| 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 | Asymmetric synthesis | |
| dc.title | Asymmetric total syntheses of (+)- and (-)-spirotryprostatins A and B | |
| 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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