Bromonium-Initiated Epoxide-Opening Cascades : total Synthesis of ent-Dioxepandehydrothyrsiferol and Synthetic Studies toward (+)-Scholarisine A
Thesis (Ph. D. in Organic Chemistry)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013.
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| Format: | Thesis |
| Language: | eng |
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Massachusetts Institute of Technology
2013
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| Online Access: | http://hdl.handle.net/1721.1/79260 |
| _version_ | 1826204620341379072 |
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| author | Tanuwidjaja, Jessica |
| author2 | Timothy F. Jamison. |
| author_facet | Timothy F. Jamison. Tanuwidjaja, Jessica |
| author_sort | Tanuwidjaja, Jessica |
| collection | MIT |
| description | Thesis (Ph. D. in Organic Chemistry)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013. |
| first_indexed | 2024-09-23T12:58:19Z |
| format | Thesis |
| id | mit-1721.1/79260 |
| institution | Massachusetts Institute of Technology |
| language | eng |
| last_indexed | 2024-09-23T12:58:19Z |
| publishDate | 2013 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/792602019-04-11T03:22:01Z Bromonium-Initiated Epoxide-Opening Cascades : total Synthesis of ent-Dioxepandehydrothyrsiferol and Synthetic Studies toward (+)-Scholarisine A Total Synthesis of ent-Dioxepandehydrothyrsiferol and Synthetic Studies toward (+)-Scholarisine A Tanuwidjaja, Jessica Timothy F. Jamison. Massachusetts Institute of Technology. Department of Chemistry. Massachusetts Institute of Technology. Department of Chemistry. Chemistry. Thesis (Ph. D. in Organic Chemistry)--Massachusetts Institute of Technology, Dept. of Chemistry, 2013. Vita. Cataloged from PDF version of thesis. Includes bibliographical references. CHAPTER I. Bromonium-Initiated Epoxide-Opening Cascades: Total Synthesis of ent-Dioxepandehydrothyrsiferol Our foray into the total synthesis of ent-dioxepandehydrothyrsiferol has led to the discovery and development of the bromonium-initiated epoxide-opening cascade. This transformation constructs the signature trans-anti-trans tricyclic portion of the natural product containing the bromo-oxepane in a single step. Further explorations into this cascade also revealed feasibility of incorporation of exogenous trapping nucleophiles into the reaction. [chemical formulae] CHAPTER 11. Synthetic Studies toward (+)-Scholarisine A. A concise and scalable route toward the monoterpene indole alkaloid (+)- scholarisine A has been developed. Synthetic highlights of the route include: 1) cisselective Diels-Alder cycloaddition reaction to construct strained 5,6-fused hydrindanones, 2) a novel indole formation via an in-situ aza-Wittig reaction, and 3) a selective enolization and hydrolysis sequence of a diketone substrate to provide rapid access to a key tetracyclic intermediate. Studies to access the natural product via latestage intramolecular indole alkylations are presented. [chemical formulae] by Jessica Tanuwidjaja. Ph.D.in Organic Chemistry 2013-06-17T19:51:18Z 2013-06-17T19:51:18Z 2013 2013 Thesis http://hdl.handle.net/1721.1/79260 846590192 eng M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission. http://dspace.mit.edu/handle/1721.1/7582 358 p. application/pdf Massachusetts Institute of Technology |
| spellingShingle | Chemistry. Tanuwidjaja, Jessica Bromonium-Initiated Epoxide-Opening Cascades : total Synthesis of ent-Dioxepandehydrothyrsiferol and Synthetic Studies toward (+)-Scholarisine A |
| title | Bromonium-Initiated Epoxide-Opening Cascades : total Synthesis of ent-Dioxepandehydrothyrsiferol and Synthetic Studies toward (+)-Scholarisine A |
| title_full | Bromonium-Initiated Epoxide-Opening Cascades : total Synthesis of ent-Dioxepandehydrothyrsiferol and Synthetic Studies toward (+)-Scholarisine A |
| title_fullStr | Bromonium-Initiated Epoxide-Opening Cascades : total Synthesis of ent-Dioxepandehydrothyrsiferol and Synthetic Studies toward (+)-Scholarisine A |
| title_full_unstemmed | Bromonium-Initiated Epoxide-Opening Cascades : total Synthesis of ent-Dioxepandehydrothyrsiferol and Synthetic Studies toward (+)-Scholarisine A |
| title_short | Bromonium-Initiated Epoxide-Opening Cascades : total Synthesis of ent-Dioxepandehydrothyrsiferol and Synthetic Studies toward (+)-Scholarisine A |
| title_sort | bromonium initiated epoxide opening cascades total synthesis of ent dioxepandehydrothyrsiferol and synthetic studies toward scholarisine a |
| topic | Chemistry. |
| url | http://hdl.handle.net/1721.1/79260 |
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