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Development of Novel Fluorous Tagging Reagents and Progress Towards (4S,8S,12S)-4,8,12-Trimethylnonadecanol

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 (Unpublished)

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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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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Budavich, Owen Wowb3@pitt.eduOWB3
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairCurran, Dennis Pcurran@pitt.eduCURRAN
Committee MemberNelson, Scott Gsgnelson@pitt.eduSGNELSON
Committee MemberLiu, Xinyuxinyuliu@pitt.eduXINYULIU
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


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