Page 1 |
Save page Remove page | Previous | 1 of 184 | Next |
|
small (250x250 max)
medium (500x500 max)
large ( > 500x500)
Full Resolution
All (PDF)
|
This page
All
Subset |
AN ORGANIC CHEMISTRY APPROACH TOWARD THE SYNTHESIS OF
VALUABLE BIOLOGICAL COMPOUNDS: SYNTHETIC PROGRESS TOWARD
THE PALMEROLIDE A SUBUNITS, EXPEDITIOUS ENYNE COUPLING VIA
ALKYNES, AND DEVELOPMENT OF THE NEXT GENERATION OF HIV-1
INTEGRASE INHIBITORS
by
Victor Hadi
____________________________________________________________
A Dissertation Presented to the
FACULTY OF THE USC GRADUATE SCHOOL
UNIVERSITY OF SOUTHERN CALIFORNIA
In Partial Fulfillment of the
Requirements for the Degree
DOCTOR OF PHILOSOPHY
(CHEMISTRY)
December 2010
Copyright 2010 Victor Hadi
Object Description
| Title | An organic chemistry approach toward the synthesis of valuable biological compounds: synthetic progress toward the Palmerolide A subunits, expeditious enyne coupling via alkynes, and development of the next generation of HIV-1 integrase inhibitors |
| Author | Hadi, Victor |
| Author email | victorhadi@gmail.com; vhadi@usc.edu |
| Degree | Doctor of Philosophy |
| Document type | Dissertation |
| Degree program | Chemistry |
| School | College of Letters, Arts and Sciences |
| Date submitted | 2010 |
| Restricted until | Unrestricted |
| Date published | 2010-11-30 |
| Advisor (committee chair) | Jung, Kyung Woon |
| Advisor (committee member) |
Prakash, G. K. Surya Neamati, Nouri |
| Abstract | A very rare opportunity has been bestowed into me to work in three different facets of organic chemistry: total synthesis, methodology, and medicinal chemistry. While this intensive experience has certainly assisted me to become a better scientist, there are still many more tasks for me to accomplish. Still, I am confident that my PhD training has prepared me to embark upon the world ahead.; In chapter 1 of this thesis, I will describe the synthetic progress of two subunits, which can be coupled to make a macrolide called Palmerolide A, a bioactive molecule targeting melanoma (i.e. skin cancer). The synthesis of the first subunit is almost complete and it proceeds without significant deviation from the originally proposed scheme. The synthesis of the second subunit is halfway complete. Sensitive functional groups in the second subunit have made it more challenging to complete this piece of Palmerolide A.; A major challenge faced in the preparation of Palmerolide A was the macrocyclization step. Although the boron-Heck reaction did not work successfully for macrocyclization of Palmerolide A, various aspects of this methodology have come to surface. While working on several different coupling reactions for the total synthesis project, I had a chance to explore different aspects of an sp-sp² boron-Heck coupling reaction, which will be described in detail in Chapter 2.; Chapter 3 details a collaborative project between my advisor and a colleague of his toward the synthesis of the next generation HIV-1 integrase inhibitors. Utilizing focus alteration strategy, an unexpected hit compound has been optimized into a marginally more potent integrase inhibitor. |
| Keyword | enyne formation; integrase inhibitor; Palmerolide A; pyrazolone |
| Language | English |
| Part of collection | University of Southern California dissertations and theses |
| Publisher (of the original version) | University of Southern California |
| Place of publication (of the original version) | Los Angeles, California |
| Publisher (of the digital version) | University of Southern California. Libraries |
| Provenance | Electronically uploaded by the author |
| Type | texts |
| Legacy record ID | usctheses-m3569 |
| Rights | Hadi, Victor |
| Repository name | Libraries, University of Southern California |
| Repository address | Los Angeles, California |
| Repository email | http://www.usc.edu/isd/libraries/services/ask_a_librarian/email/ |
| Filename | etd-Hadi-4188 |
| Archival file | uscthesesreloadpub_Volume23/etd-Hadi-4188.pdf |
Description
| Title | Page 1 |
| Full text | AN ORGANIC CHEMISTRY APPROACH TOWARD THE SYNTHESIS OF VALUABLE BIOLOGICAL COMPOUNDS: SYNTHETIC PROGRESS TOWARD THE PALMEROLIDE A SUBUNITS, EXPEDITIOUS ENYNE COUPLING VIA ALKYNES, AND DEVELOPMENT OF THE NEXT GENERATION OF HIV-1 INTEGRASE INHIBITORS by Victor Hadi ____________________________________________________________ A Dissertation Presented to the FACULTY OF THE USC GRADUATE SCHOOL UNIVERSITY OF SOUTHERN CALIFORNIA In Partial Fulfillment of the Requirements for the Degree DOCTOR OF PHILOSOPHY (CHEMISTRY) December 2010 Copyright 2010 Victor Hadi |
Comments
Post a Comment for Page 1
