Progress toward an asymmetric total synthesis of the Stemona alkaloid tuberostemoninol
| dc.contributor.author | Jia, Xiangna, author | |
| dc.contributor.author | Williams, Robert M., advisor | |
| dc.date.accessioned | 2022-11-28T17:46:48Z | |
| dc.date.available | 2022-11-28T17:46:48Z | |
| dc.date.issued | 2009 | |
| dc.description.abstract | Presented herein is a twenty-five linear step synthetic progress toward an asymmetric total synthesis of the Stemona alkaloid tuberostemoninol. A diastereoselective intramolecular Pauson-Khand reaction of a glycinate derivative served to construct the BC ring system and set one of the two quaternary carbon centers present in the target molecule in high yield. The γ-lactone E ring and azepine D ring were constructed subsequently. Several approaches were explored for the introduction of the γ-lactone E ring carbon skeleton containing the α-methylene group. Further elaboration of the BCDE tetracycle toward tuberostemoninol was performed to afford the corresponding ketone compound, which makes completion of the total synthesis possible in ten steps. | |
| dc.format.medium | doctoral dissertations | |
| dc.identifier.uri | https://hdl.handle.net/10217/235857 | |
| dc.language | English | |
| dc.language.iso | eng | |
| dc.publisher | Colorado State University. Libraries | |
| dc.relation | Catalog record number (MMS ID): 991011858139703361 | |
| dc.relation | QD421.J532 2009 | |
| 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 | Alkaloids -- Synthesis | |
| dc.subject.lcsh | Organic compounds -- Synthesis | |
| dc.title | Progress toward an asymmetric total synthesis of the Stemona alkaloid tuberostemoninol | |
| 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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