Studies on the total synthesis of putative intermediates in the biosynthesis of taxol
| dc.contributor.author | Lenger, Steven Robert, 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 exploration of several strategies for the synthesis of taxoids useful for studying the biosynthesis of taxol is presented. The approaches described include attempts to access the taxane carbon skeleton through closure of the B-ring across the C-2 – C-3 bond or the C-10 – C-11 bond, as well as attempts to form the A- and B-rings using an intramolecular Diels-Alder reaction. Attempts to close the C-2 – C-3 bond employed an ally! silane to attack either a ketone, aldehyde, or acetal to close the B-ring in an intramolecular Sakurai reaction. The preparation of four substrates suited to undergo this type of ring closure is described. Attempts to close the B-ring across the C-10 – C-11 bond focused on converting a vinyl halide to the corresponding vinyl chromium or vinyl palladium and closing the Bring through either a Nozaki-Hiyama-Kishi reaction or a Heck reaction. The preparation of six substrates suited to undergo ring closure through this means is described. Attempts to form the A- and B-rings using an intramolecular Diels-Alder reaction were made. The preparation of three substrates suited to undergo ring closure through this means is described. | |
| dc.format.medium | doctoral dissertations | |
| dc.identifier.uri | https://hdl.handle.net/10217/235863 | |
| dc.language | English | |
| dc.language.iso | eng | |
| dc.publisher | Colorado State University. Libraries | |
| dc.relation | Catalog record number (MMS ID): 991018481179703361 | |
| dc.relation | RC271.T38L45 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.lcsh | Paclitaxel -- Synthesis | |
| dc.title | Studies on the total synthesis of putative intermediates in the biosynthesis of taxol | |
| 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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