| NSF Org: |
CHE Division Of Chemistry |
| Recipient: |
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| Initial Amendment Date: | April 1, 2016 |
| Latest Amendment Date: | July 10, 2018 |
| Award Number: | 1565500 |
| Award Instrument: | Standard Grant |
| Program Manager: |
Jin Cha
CHE Division Of Chemistry MPS Directorate for Mathematical and Physical Sciences |
| Start Date: | May 1, 2016 |
| End Date: | May 31, 2019 (Estimated) |
| Total Intended Award Amount: | $450,000.00 |
| Total Awarded Amount to Date: | $545,745.00 |
| Funds Obligated to Date: |
FY 2017 = $52,219.00 FY 2018 = $43,526.00 |
| History of Investigator: |
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| Recipient Sponsored Research Office: |
845 N PARK AVE RM 538 TUCSON AZ US 85721 (520)626-6000 |
| Sponsor Congressional District: |
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| Primary Place of Performance: |
Tucson AZ US 85721-0001 |
| Primary Place of
Performance Congressional District: |
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| Unique Entity Identifier (UEI): |
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| Parent UEI: |
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| NSF Program(s): |
OFFICE OF MULTIDISCIPLINARY AC, Chemical Synthesis |
| Primary Program Source: |
01001718DB NSF RESEARCH & RELATED ACTIVIT 01001819DB NSF RESEARCH & RELATED ACTIVIT |
| Program Reference Code(s): |
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| Program Element Code(s): |
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| Award Agency Code: | 4900 |
| Fund Agency Code: | 4900 |
| Assistance Listing Number(s): | 47.049 |
ABSTRACT
The Chemical Synthesis Program of the NSF Chemistry Division supports the research of Professor Jon T. Njardarson in the Department of Chemistry and Biochemistry at the University of Arizona. Heterocyclic compounds are one of the more important structural scaffolds found in pharmaceuticals while also playing key roles in numerous other material applications. Professor Njardarson and his students develop useful new cascade reactions to make pharmaceuticals. For each one of these new cascade reactions, two simple and readily accessible building blocks are brought together in such a way that valuable complex chiral products result. In addition, this project provides excellent training of undergraduate and graduate students. Particularly noteworthy deliverables, which the students associated with these projects are involved in, are unique freely accessible educational/research tools such as pedagogical tools for structure elucidation, the free mobile app/website Chemistry By Design and, novel pharmaceutical structure analyses.
The new heterocyclic methods developed in this award provide researchers in the pharmaceutical industry with new and complementary approaches for building important structures. Through the use of cascade reactions, the researchers make innovative contributions to the asymmetric syntheses of valuable heterocyclic ring structures while establishing new knowledge in the areas of a) anionic isomerizations, b) anion accelerated rearrangements, c) ring expansion reactions, d) strain assisted rearrangements, and e) asymmetric dipolar cycloaddition reactions. The many reactions emerging from this research program open the door for researchers in academia and industry to develop useful new blueprints for their target oriented synthesis pursuits. These new classes of reactions, which employ bi-functional nucleophiles, promise to be of broad scope and highly tunable. Particular focus is on elucidating and understanding the reaction mechanisms so that the resulting knowledge foundation can aid in designing new reactions and opening new avenues of investigation. These new educational products provide students, researchers and the public with new opportunities to learn about organic chemistry and its importance to society.
PUBLICATIONS PRODUCED AS A RESULT OF THIS RESEARCH
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PROJECT OUTCOMES REPORT
Disclaimer
This Project Outcomes Report for the General Public is displayed verbatim as submitted by the Principal Investigator (PI) for this award. Any opinions, findings, and conclusions or recommendations expressed in this Report are those of the PI and do not necessarily reflect the views of the National Science Foundation; NSF has not approved or endorsed its content.
This project has resulted in eight peer reviewed publications to date, which detail novel contributions in the areas of 1) new chemical reactions in the area of asymmetric anionic cascades, 2) natural product syntheses and 3) first of their kind pharmaceutical structure analyses. Anionic cascades are chemical reactions wherein multiple productive chemical bond forming events take place in one reaction. Asymmetry refers to handedness or chirality and is a centrally important feature of biological molecules and pharmaceuticals. New reactions that enable streamlined assembly of molecules, via approaches such as anionic cascades, coupled with the selective delivery of chiral products are of high value. During the grant period, several new asymmetric anionic cascades have been designed, developed and evaluated including applications towards natural product architectures. Investigations have also resulted in exciting unexpected discoveries, which have resulted in new avenues of investigations. Three graduate students have completed and defended their doctoral theses during the grant period and multiple undergraduate students have gathered invaluable independent scientific research experiences enabled by this grant support. On the chemical education front, new versions of the groups nationally and internationally recognized Top 200 Pharmaceutical posters (https://njardarson.lab.arizona.edu/content/top-pharmaceuticals-poster) were created and posted online for everyone to enjoy. The custom pharmaceutical analyses that were completed and published are a direct outgrowth from the pharmaceutical poster project. Furthermore, new content for the popular free application (app) and website (http://chemistrybydesign.oia.arizona.edu/) Chemistry By Design has been increased 30% with the database now containing 2076 natural product and pharmaceutical syntheses for anyone to peruse and learn from.
Last Modified: 06/03/2019
Modified by: Jon T Njardarson
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