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Synthesis of Spliceostatin E and Decytospolide A and B and Progress Toward the Synthesis of Thailanstatin A
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| 자료유형 | 학위논문 |
|---|---|
| 서명/저자사항 | Synthesis of Spliceostatin E and Decytospolide A and B and Progress Toward the Synthesis of Thailanstatin A. |
| 개인저자 | Veitschegger, Anne M. |
| 단체저자명 | Purdue University. Chemistry. |
| 발행사항 | [S.l.]: Purdue University., 2018. |
| 발행사항 | Ann Arbor: ProQuest Dissertations & Theses, 2018. |
| 형태사항 | 169 p. |
| 기본자료 저록 | Dissertations Abstracts International 81-02B. Dissertation Abstract International |
| ISBN | 9781085575614 |
| 학위논문주기 | Thesis (Ph.D.)--Purdue University, 2018. |
| 일반주기 |
Source: Dissertations Abstracts International, Volume: 81-02, Section: B.
Advisor: Ghosh, Arun K. |
| 이용제한사항 | This item must not be sold to any third party vendors.This item must not be added to any third party search indexes. |
| 요약 | The first stereoselective total synthesis of spliceostatin E has been accomplished. The left hand 灌-lactone subunit was constructed from commercially available (R)-glycidyl alcohol through a ring-closing metathesis as the key reaction. The central-functionalized tetrahydropyran ring was synthesized as done in the synthesis of spliceostatin A. An olefin cross-metathesis of the 灌-lactone and the central tetrahydropyran ring provided spliceostatin E. Spliceostatin E was originally reported to exhibit potent antitumor activity, however, our biological evaluation of synthetic spliceostatin E revealed that it did not inhibit in vitro spicing and did not impact speckle morphology in cells.A stereoselective total synthesis of thailanstatin A methyl ester, a semi-synthetic derivative of the natural product thailanstatin A, has been achieved. By synthesizing thailanstatin A methyl ester, we were only one step away from making the natural product, however, after many attempts, we were unable to successfully purify thailanstatin A. Both the left-hand and the central tetrahydropyran ring were constructed from readily available tri-O-acetyl-D-glucal. Notable reactions in this synthesis include a stereoselective allylation, a directed epoxidation, a Claisen rearrangement and a substrate-controlled asymmetric Michael addition. Thailanstatin A and thailanstatin A methyl ester were both originally reported to possess potent antitumor activity, with thailanstatin A methyl ester exhibiting greater potency of the two. A biological evaluation of thailanstatin A methyl ester is currently underway.A stereoselective total synthesis of the small natural products decytospolide A and B was accomplished. The synthesis features a Friedel-Crafts acylation, an asymmetric Noyori transfer hydrogenation, and an Achmatowicz rearrangement as the key reactions. A discovered concomitant reduction to directly provide the reduced tetrahydropyran ring shortened the synthesis. |
| 일반주제명 | Chemistry. |
| 언어 | 영어 |
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