Form Approved Through 09/30/2011 OMR nnn ,',,,'n wepoitmerit w mewl anti nurneri OCIVIceb 2,": Health Service is .1 • Council: 05/2009 Pt: OLSON, ANGELA C anal Researchi lkYviL i 1 F31 GM089137-01 12150871 mrship Applicatio Dual: • .„,.. ,,,struchons carefully, ReCeiVed 2116/2008 -- ' Do not exceed character length restrictions indicated IRO: ZRG1 CB-N(29) L 1. TITLE OF RESEARCH TRAINING PROPOSAL (Co not exceed 81 char Catalytic Asymmetric Synthesis of Vinyl Chromans Using Palladium(II) Catalysts 2. LEVEL OF 3. RESPONSE TO SPECIFIC REQUEST FOR APPLICATIONS OR PROGRAM ANNOUNCEMENT 0 NO N1 YES FELLOWSHIP (If "Yes,' state number and (itle) Predoctoral Number, PA-07-106 Title: Ruth L. Kirschstein National Research Service Awards for Individual Predoctoral Fellowships (F31) to Promote Diversity in Health-Related Research 4a. NAME OF APPLICANT (Last, First, Middle) 4b, ERA COMMONS USER NAME ac HIGHEST DEGREE(S) Olson, Angela, Christine B.S. I 1 4d. PRESENT MAILING ADDRESS (Street, City State Zip Code) 4e PERMANENT MAILING ADDRESS (Stre t, City, State, Zip Code) Of E-MAIL ADDRESS: TELEPHONES AND FAX (Area code, number and extension) 4 OFFICE 4h HOME 4i PERMANENT 41. FAX NUMBER 949-824-9017 949-824-3866 4 5. TRAINING UNDER PROPOSED AWARD (See Fields of I raining) b. PHIQR AND/OR LURREN I NRSA SUPPOR I (Individual or Institutional) Di cipline No : Subcategory Name: le NO . YES (If 'Yes,' refer to item 22 Form Page 5) 1770 Synthetic Chemistry 7a, DATES OF PROPOSED AWARD Th. PROPOSED AWARD DURATION 8, DEGREE SOUGHT DURING PROPOSED AWARD From (MM/DD/YY): Through (MM/DD/YY): (in months) Degree Expected Completion Date: 07/01/09 06/30/12 36 Ph.D. 06/2012 9, HUMAN SUBJECTS 9b Federalwde Assurance Na RESEARCH N/A 10. VERTEBRATE ANIMALS EE No 0 Yes El No 0 Yes 10a. Animal Welfare Assurance No. 0 Indefinite ' 9c. Clinical Trial 90. NIH-delined Phase III rE No 0 Yes Chrocal Trial E1 No 0 Yes NIA 9a. Research Exempt El No 0 Yes If 'Yes,' Exemption No. N/A 11. SPONSORING INSTITUTION IS. OFFICIAL SIGNING FOR SPONSORING INSTITUTION Name Regents, University of California Name Judith Aguirre Address Sponsored Projects Administration Title Contract and Grant Officer University of California, Irvine Address Sponsored Projects Administration 300 University Tower University of California, Irvine Irvine, CA 92697-7600 300 University Tower Irvine, CA 92697-7600 12a. ENTITY IDENTIFICATION NO. 12b. DUNS NO. Tel: (949) 824-0446 Fax: (949) 824-2094 1-95-2226406-A1 04-670-5849 E-Mail: [email protected] 14. APPLICANT ORGANIZATION CERTIFICATION AND ACCEPTANCE: I certify that the statements herein are true, complete, and a curate to the best of my knowledge, and I agree to comply with the terms and conditions of award if an ward is. issued as a resuJt of this ipplicationriar aware that any falsp, fictitious, or fraudulent statements or clams may subject me to criminal, civil, or administrative penalties. th (1.1Q.-1/5r7L, //(C/Dg SIGNATURE OF OFFICIAL NAMED IN 13. DATE ,.......------ \ (In ink Per signature not acceptable.) 1 1- 9-09 PHS 016-1 Rev. 9/08) Face Pagyudith pone Form Page 1 Contract & Grant Officer NAME OF APPLICANT (Last, first, middle initial) Kirschstein-NRSA Individual Fellowship Application Olson, Angela, C. (To be completed by applicant— follow P1-IS 416-1 instructions) SPONSOR and Co-Sponsor' formation 15 NAME OF SPONSOR 16. NAME OF Co-SPONSOR (VVhen applicable) 15a. NAME AND DEGREE(S) 16a NAME AND DEGREE(S) Professor Larry E. Overman, Ph.D. N/A 15b. ERA COMMONS USER NAM: 16b. ERA COMMONS USER NAME 15c DEPARTMENT, SERVICE, LABORATORY, OR EQUIVALENT 16c. DEPARTMENT, SERVICE, LABORATORY, OR EQUIVALENT Chemistry 15d. MAJOR SUBDIVISION 16d. MAJOR SUBDIVISION Physical Sciences 15e. Address: 16e Address: University of California, Irvine Chemistry Department 1102 Natural Sciences 2 Irvine, CA 92697-2025 Telephone: Telephone Far Fax: E-Mail E-Mail: RESEARCH PROPOSAL 17. DESCRIPTION: See instructions. State the applications broad, Ion -term objectives and specific aims, making reference to the health relatedness of the project (I e . relevance to the mission of the agency) Describe conciseN the research design and methods for achieving these goals. Describe the rationale and techniques you will use to pursue the e goals. In addition. in two or three sentences, describe m plain, lay language t e relevance of this research to public health. If the application is funded, this description, as is, will become public information. Therefore, do not include proprietary/confidential information. DO NOT EXCEED EDE SPACE PROVIDED. The proposal describes the development of a mild and efficient method for the catalytic asymmetric synthesis of vinyl chromans. The chroman motif is present in numerous small molecules of biological importance and the current methods available to access these substrates are limited. The SN2' allylic substitution chemistry of trichloroacetimidates using a tethered phenol nucleophile will be examined using chiral cobalt oxazoline palladium(11) catalysts. An efficient and convergent method to access a variety of key cyclization substrates will be developed. The scope of functional groups and substitution patterns compatible with this system will be explored. A variety of heterocycles with important biological activity may also be synthesized using this chemistry. This methodology will allow easy access to a broader range of biologically active small molecules and their analogues. This proposal describes the development of a general method to access biologically important small molecules in a selective manner. This methodology will be beneficial to the synthetic community because a vast number of small molecules and their analogues will be readily available and their biological activity can be explored. PhIS 416-1 (Rev 9/08) Page 2 Number pages consecutmety at The bottom throughout Form Page 2 the application Do not use Suffixes such as 2a, 2e Kirschstein-NRSA Individual Fellowship Application NAME OF APPLICANT (Last, first, middle initial) Olson. Angela, a (To be completed by applicant- follow PHS 016-1 instructions) 18. GOALS FOR KIRSCHSTEIN-NRSA FELLOWSHIP TRAINING AND CAREER My main interest in research is the development of novel methodology and its application in organic synthesis. Currently, my specific area of research focuses on intramolecular reactions of allylic trichloroacetimidates. I hope to expand upon the cobalt oxazoline palladacycle-catalyzed SN2' allylic substitution reactions that have been developed in our group_ By studying these new reactions, I hope to gain new insight into these types of transformations and develop new tools for the synthetic community. During my graduate studies, I would like to further develop my research skills by learning new techniques and improving my ability to approach, analyze, and solve problems in organic chemistry. I am interested in applications of organic chemistry in a government laboratory setting. I would like to contribute to the well- being and health of our society through research and development. 19.ACTIVITIES PLANNED UNDER THIS AWARD. Approximate percentage of proposed award time in activities identified below. (See instructions) Year Research Course Work Teaching Clinical First 100% Second 100% Third 100% PREDOCTORAL FELLOWSHIPS ONLY Fourth Fifth MD/PhD FELLOWSHIPS 0 JLY Sixth Briefly explain activities other than research and relate them to the proposed research training N/A 20. TRAINING SITE(S) Is the Primary Training Site the same as the Sponsoring Institution, 0 Yes E No If No, provide detailed information below for the Primary Training Site Location Organizational Name: DUNS: Street 1: Street 2 City. County. State: Province: Country. Zip/Postal Code. Project/Performance Site Congressional Districts: 21 HUMAN EMBRYONIC STEM CELLS 2 No . Yes If the proposed project involves human embryonic stem cells, list below the registration number of the specific cell line(s) from the following list: http://stemcells.mhmov/research/recustrv/eliqibilityCriteria.asp. Use continuation pages as needed. If a specific line cannot be referenced at this time, include a statement that one from the Registry will be used. Cell Line PBS 416-1 (Rev. 9/08) Page 3 Form Page 3 Kirschstein-NRSA Individual Fellowship Application NAME OF APPLICANT (Lest first, middle Table of Contents Olson, Angela, C. Page Numbers (Number pages consecutively at the bottom throughout Section I — Applicant/Fellow the application. Do not use suffixes such as 6a, 6b) Face Page 1 Sponsor's Contact Information, Description (Form Page 2) 2 Training & Career Goals, Activities Planned Under This Award, Training Site(s), Human Embryonic Stem Cells (Form Page 3) 3 Table of Contents (Form Page 4) 4 Biographical Sketch - ApplicanVFellow (Not to exceed four pages) 5-6 Previous Research Experience (Form Page 5) 7 Research Training Plan 1. Introduction to Resubmission Application (not to exceed I page) N/A 2. Specific Aims 8 3, Background/Significance (Items 2-5 not to exceed 10 pages) 8-11 4. Preliminary Studies/Progress Report 11-12 5. Research Design and Methods 12-15 6. Inclusion Enrollment Report (for Renewal applications only) N/A 7. Progress Report Publication List (for Renewal applications only) N/A 8. Human Subjects (Required if Item 9 on the Face Page is marked "Yes') N/A 9. Clinical Trial N/A 10. Agency-Defined Phase Ill Clinical Trial N/A 11. Protection of Human Subjects (Required if Item 9 on the Face Page is marked "Yes") N/A 12. Inclusion of Women and Minorities (Required if Item 9 on the Face Page is marked "Yes" and is Clinical Research) N/A 13. Targeted/Planned Enrollment Table (for new and continuing clinical research studies) N/A 14. Inclusion of Children (Required if Item 9 on the Face Page is marked "Yes') N/A 15. Vertebrate Animals (Required if item 10 on the Face Page is marked "Yes') N/A 16. Select Agent Research N/A 17, Literature Cited 15-16 18. Resource Sharing N/A 19.