Total synthesis of Zoanthamine

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18. GOALS FOR FELLOWSHIP TRAINING AND CAREER The primary goal for my training is to learn the necessary skills to become an excellent organic chemist who can teach organic chemistry at the university level and can conduct research independently. The Theodorakis' laboratory nurtures new ideas and encourages the development of new methodologies in organic synthesis. This approach will enhance my understanding chemical reactivity. The weekly research meetings of the Theodorakis' group during which every student presents a thorough explanation of their ongoing research will help me practice my teaching skills and to develop a better understanding of chemistry. In addition, the correlation between organic chemistry and biology is constantly discussed in order to better understand the biological mode of action of different molecules. This project will expose me to as much chemistry as needed to succeed in the laboratory as well as in the classroom. This fellowship would enable me to accomplish my career goals which are to complete my Ph. D to ultimately teach at the university level and set a role model to disadvantaged minority groups 19. NAME AND DEGREE(S) Emmanuel Theodorakis, 20. POSITION/RANK University of California, San 21. RESEARCH INTERESTS/AREAS Total Synthcsis of Natural Products and Drug Design 22. DESCRIPTION (Do not exceed space provided) SPONSOR Doctorate degree in Organic Chemistry Diego Organic Chemistry Professor i| _tl _;1 ",'ol"n -,,-Il_o]llo]-'_'i_l Our goal is to develop a feasible synthetic procedure that can yield Zoanthamine and other members of this alkaloid family such as norzoanthamine in a concise manner. Most of these alkaloids possess highly functionalized trans-decalone and heterocyclic aminal ring system along with at least three quaternary chiral centers (C-9, C-12, C-22 for zoanthamine). Zoanthamine and its relatives were found to inhibit phorbol myristate acetate induced inflammation in a model system. Norzoanthamine was found to inhibit the growth of P388 murine leukemia cell cultures. In addition, norzoanthamine inhibits IL-6 production. Recently, it has been reported that zoanthamine-type alkaloids suppress the decrease in bone weight. The construction of the core of zoanthamine will lead us to hopefully develop a library of its analogs to further study their potential as candidates for an osteoporotic drug and/or an anti-inflammatory drug. PHS 416-1 (Rev. 12/98) Form Page 2 BB co NAME(Last, first,middle initial) Individual NRSA Application Rivas, Fatima, R Tabte of Contents Page Numbers (Numberpagesconsecutively at thebottomthroughouthe applicationD. onotuse Section I-Applicant suffixesuchas5a, 5b.) Face Page (Items 1-8, 15), Form Page 2 (items 16-18, 22), and Table of Contents ========================================Section End===========================================