Budavich, Owen W
(2015)
Development of Novel Fluorous Tagging Reagents and Progress Towards (4S,8S,12S)-4,8,12-Trimethylnonadecanol.
Master's Thesis, University of Pittsburgh.
(Unpublished)
Abstract
The configuration of methyl groups within polyisoprenoid motifs of natural products continue to be difficult to assign. The syn/anti relationships of methyl groups within oligoisoprenoids have been shown to produce reliable differences in 1H and 13C NMR spectra. However, the data set requires expanion to include longer polyisoprenoid motifs and the stereopurity of these samples needs to be higher.
Herein, we describe the advancements towards making a more comprehensive data set of oligoisoprenoids in high stereopurity through a fluorous mixture synthesis. Four new fluorous tagging reagents were synthesized and demonstrated to separate otherwise identical compounds. From which a simple method was developed to evaluate the potential of future fluorous tags. Additionally, the known reaction conditions for aryl thionocarbonate ester formation were optimized to reduce the presence of byproduct; increasing the isolatable yield. Finally, an iterative reaction scheme utilizing a highly selective (96 % de, +99 % ee) iridium catalyzed crotylation reaction was used towards the synthesis of (4S,8S,12S)-4,8,12,-trimethyl-nonadecanol.
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Details
| Item Type: |
University of Pittsburgh ETD
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| Status: |
Unpublished |
| Creators/Authors: |
| Creators | Email | Pitt Username | ORCID  |
|---|
| Budavich, Owen W | owb3@pitt.edu | OWB3 | |
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| ETD Committee: |
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| Date: |
9 January 2015 |
| Date Type: |
Publication |
| Defense Date: |
15 August 2014 |
| Approval Date: |
9 January 2015 |
| Submission Date: |
14 August 2014 |
| Access Restriction: |
No restriction; Release the ETD for access worldwide immediately. |
| Number of Pages: |
206 |
| Institution: |
University of Pittsburgh |
| Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
| Degree: |
MS - Master of Science |
| Thesis Type: |
Master's Thesis |
| Refereed: |
Yes |
| Uncontrolled Keywords: |
Fluorous Tags, Fluorous Mixture Synthesis, Fluorous Chemistry, Oligoisoprenoids, Crotylation |
| Date Deposited: |
09 Jan 2015 16:34 |
| Last Modified: |
15 Nov 2016 14:23 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/22726 |
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