Maciejewski, John Paul
(2011)
New Methods for Heterocycle Preparation.
Doctoral Dissertation, University of Pittsburgh.
(Unpublished)
Abstract
This dissertation will describe the development and application of novel methods for heterocycle preparation. The first chapter will outline the development of a titanocene catalyzed epoxide-opening rearrangement to prepare indolines from epoxyanilines. A discussion of the reaction development, along with the substrate scope and limitations will be reported.The second chapter will describe progress toward expanding the scope of aStaudinger/aza-Wittig reaction used to prepare substituted 1,2,4-triazines. This methodology has been applied towards the synthesis of a model system for the DEF rings of the natural product noelaquinone. The challenges associated with the Staudinger/aza-Wittig reaction, and the late-stage oxidation strategy to prepare the DEF rings of the noelaquinone model system will be discussed.The third chapter will describe the importance and general preparation of (E)-alkene peptide isosteres. Using compounds prepared in the UPCMLD and published on PubChem as a reference, we present our ongoing initiative to expand the library of α,β-cyclopropyl-γ-amino acid analogs.
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Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
| Creators | Email | Pitt Username | ORCID  |
|---|
| Maciejewski, John Paul | jpm53@pitt.edu | JPM53 | |
|
| ETD Committee: |
| Title | Member | Email Address | Pitt Username | ORCID |
|---|
| Committee Chair | Wipf, Peter | | | | | Committee Member | Day, Billy | | | | | Committee Member | Curran, Dennis | | | | | Committee Member | Floreancig, Paul | | | |
|
| Date: |
30 June 2011 |
| Date Type: |
Completion |
| Defense Date: |
3 March 2011 |
| Approval Date: |
30 June 2011 |
| Submission Date: |
30 March 2011 |
| Access Restriction: |
No restriction; Release the ETD for access worldwide immediately. |
| Institution: |
University of Pittsburgh |
| Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
| Degree: |
PhD - Doctor of Philosophy |
| Thesis Type: |
Doctoral Dissertation |
| Refereed: |
Yes |
| Uncontrolled Keywords: |
azide; radical cyclization; azaindoline; peptide mimic |
| Other ID: |
http://etd.library.pitt.edu/ETD/available/etd-03302011-150740/, etd-03302011-150740 |
| Date Deposited: |
10 Nov 2011 19:33 |
| Last Modified: |
15 Nov 2016 13:37 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/6660 |
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