dc.contributor.advisor | Williams, Robert M. |
dc.contributor.author | Rafferty, Ryan J. |
dc.contributor.committeemember | Shi, Yian |
dc.contributor.committeemember | Crans, Debbie C. |
dc.contributor.committeemember | Preito, Amy L. |
dc.contributor.committeemember | Thamm, Douglas H. |
dc.date.accessioned | 2007-01-03T05:58:42Z |
dc.date.available | 2007-01-03T05:58:42Z |
dc.date.issued | 2011 |
dc.description | 2011 Fall. |
dc.description | Includes bibliographical references. |
dc.description.abstract | Herein I discussed the total synthesis of hapalindoles J and U, the formal synthesis of hapalindole O, the proposed biosynthetic precursor to hapalindole K and efforts towards other hapalindole and ambiguine families of alkaloids. The hapalindoles and ambiguines both possess a highly functionalized 6:6:6:5, which I accessed over six synthetic steps via a developed silyl strategy with an overall 54% yield. Hapalindole J was synthesized in an overall 11% yield over eleven synthetic steps and hapalindole U in an overall 25% yield over thirteen synthetic steps from commercially available materials utilizing the silyl strategy developed. A formal synthesis of hapalindole O, intercepting Natsume's total synthesis, was accomplished as well via the developed silyl strategy. In addition, the synthesis of the proposed biosynthetic precursor to hapalindole K was accessed. Currently, this newly developed silyl strategy is being employed in accessing some of the more functionalized hapalindoles (such as K) as well as the complex ambiguine core. |
dc.format.medium | born digital |
dc.format.medium | doctoral dissertations |
dc.identifier | Rafferty_colostate_0053A_10849.pdf |
dc.identifier | ETDF2011500228CHEM |
dc.identifier.uri | http://hdl.handle.net/10217/80352 |
dc.language | English |
dc.publisher | Colorado State University. Libraries |
dc.relation.ispartof | 2000-2019 - CSU Theses and Dissertations |
dc.rights | Copyright of the original work is retained by the author. |
dc.subject | ambiguine |
dc.subject | total synthesis |
dc.subject | silyl |
dc.subject | hapalindole |
dc.title | Total synthesis of hapalindoles J and J, formal synthesis of haplaindole O, synthesis of the proposed biosynthetic precursor to hapalindole K and work towards the ambiguine family of alkaloids |
dc.type | Text |
dcterms.rights.dpla | The copyright and related rights status of this item has not been evaluated (https://rightsstatements.org/vocab/CNE/1.0/). Please refer to the organization that has made the Item available for more information. |
thesis.degree.discipline | Chemistry |
thesis.degree.grantor | Colorado State University |
thesis.degree.level | Doctoral |
thesis.degree.name | Doctor of Philosophy (Ph.D.) |