Total syntheses of (±)-fawcettimine, (±)-fawcettidine, (±)-lycoflexine, and (±)-lycoposerramine B
| dc.contributor.author | Pan, Guojun, author | |
| dc.contributor.author | Williams, Robert M., advisor | |
| dc.contributor.author | Henry, Charles, committee member | |
| dc.contributor.author | MacNeil, Maechael, committee member | |
| dc.contributor.author | Rovis, Tomislav, committee member | |
| dc.contributor.author | Wood, John L., committee member | |
| dc.date.accessioned | 2007-01-03T08:10:09Z | |
| dc.date.available | 2007-01-03T08:10:09Z | |
| dc.date.issued | 2012 | |
| dc.description.abstract | The total syntheses of (±)-fawcettimine, (±)-lycoflexine, (±)-fawcettidine, and (±)-lycoposerramine B have been accomplished through an efficient, unified, and stereocontrolled strategy that required sixteen, sixteen, seventeen, and seventeen steps, respectively, from commercially available materials. The key transformations involve: 1) a Diels-Alder reaction between a 1-siloxy diene and an enone to construct the cis-fused 6,5-carbocycles with one all-carbon quaternary center, and 2) a Fukuyama-Mitsunobu reaction to form the azonine ring. Access to the enantioselective syntheses of these alkaloids can be achieved by kinetic resolution of the earliest intermediate via a Sharpless asymmetric dihydroxylation. | |
| dc.format.medium | born digital | |
| dc.format.medium | doctoral dissertations | |
| dc.identifier | Pan_colostate_0053A_10897.pdf | |
| dc.identifier | ETDF2012400267CHEM | |
| dc.identifier.uri | http://hdl.handle.net/10217/67622 | |
| dc.language | English | |
| dc.language.iso | eng | |
| dc.publisher | Colorado State University. Libraries | |
| 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 | fawcettimine | |
| dc.subject | total synthesis | |
| dc.subject | lycoposerramine B | |
| dc.subject | lycoflexine | |
| dc.subject | lycopodium | |
| dc.subject | fawcettidine | |
| dc.title | Total syntheses of (±)-fawcettimine, (±)-fawcettidine, (±)-lycoflexine, and (±)-lycoposerramine 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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