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Progress towards the Total Synthesis of Leiodelide A
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| 자료유형 | 학위논문 |
|---|---|
| 서명/저자사항 | Progress towards the Total Synthesis of Leiodelide A. |
| 개인저자 | Ward, Sarah A. |
| 단체저자명 | Indiana University. Chemistry. |
| 발행사항 | [S.l.]: Indiana University., 2019. |
| 발행사항 | Ann Arbor: ProQuest Dissertations & Theses, 2019. |
| 형태사항 | 243 p. |
| 기본자료 저록 | Dissertations Abstracts International 81-05B. Dissertation Abstract International |
| ISBN | 9781687905376 |
| 학위논문주기 | Thesis (Ph.D.)--Indiana University, 2019. |
| 일반주기 |
Source: Dissertations Abstracts International, Volume: 81-05, Section: B.
Advisor: Williams, David R. |
| 이용제한사항 | This item must not be sold to any third party vendors. |
| 요약 | Leiodelide A is a deep-water Leiodematium (order Lithistida, family Azoricidae) sponge was isolated near the Uchelbeluu Reef in Palau, an island off the Eastern coast of the Philippines, at a 720-foot depth. This natural product is a novel 19-membered macrolactone, containing a 1,3-oxazole ring, and an 慣-hydroxy-慣-methyl carboxylic acid terminating in a 10-carbon side chain. This natural product shows cytotoxicity for human colon adenocarcinoma, leukemia, non-small cell lung cancer, and ovarian cancer. Due to the lack of natural abundance, leiodelide A is of high synthetic interest, offering important biological activity, structural complexity, an unassigned C13 stereocenter, and a possible way to determine to structure of leiodelide B through a biomimetic conversion. The following studies have developed a variable, convergent strategy for the synthesis of the entire carbon framework and late stage intermediates of leiodelide A and its derivatives. Key reactions included an effective preparation of the 2,4-disubstituted oxazole core is achieved through a halogen-dance reaction. A subsequent palladium(0) cross coupling is used to incorporate the substituted oxazole into the macrolide precursor. The chiron approach is used to incorporate the variable R- or S-C13, and subsequent MacMillan organocatalysis effectively incorporates the C15 oxygenated stereocenter. A sulfone displacement successfully unites the carbon skeleton of the macrolide. |
| 일반주제명 | Organic chemistry. Chemistry. |
| 언어 | 영어 |
| 바로가기 | 
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