| LDR | | 00000nam u2200205 4500 |
| 001 | | 000000436769 |
| 005 | | 20200228152752 |
| 008 | | 200131s2018 ||||||||||||||||| ||eng d |
| 020 | |
▼a 9781085575614 |
| 035 | |
▼a (MiAaPQ)AAI10748498 |
| 040 | |
▼a MiAaPQ
▼c MiAaPQ
▼d 247004 |
| 082 | 0 |
▼a 540 |
| 100 | 1 |
▼a Veitschegger, Anne M. |
| 245 | 10 |
▼a Synthesis of Spliceostatin E and Decytospolide A and B and Progress Toward the Synthesis of Thailanstatin A. |
| 260 | |
▼a [S.l.]:
▼b Purdue University.,
▼c 2018. |
| 260 | 1 |
▼a Ann Arbor:
▼b ProQuest Dissertations & Theses,
▼c 2018. |
| 300 | |
▼a 169 p. |
| 500 | |
▼a Source: Dissertations Abstracts International, Volume: 81-02, Section: B. |
| 500 | |
▼a Advisor: Ghosh, Arun K. |
| 502 | 1 |
▼a Thesis (Ph.D.)--Purdue University, 2018. |
| 506 | |
▼a This item must not be sold to any third party vendors. |
| 506 | |
▼a This item must not be added to any third party search indexes. |
| 520 | |
▼a 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. |
| 590 | |
▼a School code: 0183. |
| 650 | 4 |
▼a Chemistry. |
| 690 | |
▼a 0485 |
| 710 | 20 |
▼a Purdue University.
▼b Chemistry. |
| 773 | 0 |
▼t Dissertations Abstracts International
▼g 81-02B. |
| 773 | |
▼t Dissertation Abstract International |
| 790 | |
▼a 0183 |
| 791 | |
▼a Ph.D. |
| 792 | |
▼a 2018 |
| 793 | |
▼a English |
| 856 | 40 |
▼u http://www.riss.kr/pdu/ddodLink.do?id=T15490273
▼n KERIS
▼z 이 자료의 원문은 한국교육학술정보원에서 제공합니다. |
| 980 | |
▼a 202002
▼f 2020 |
| 990 | |
▼a ***1816162 |
| 991 | |
▼a E-BOOK |