| LDR | | 00000nam u2200205 4500 |
| 001 | | 000000433083 |
| 005 | | 20200225112024 |
| 008 | | 200131s2019 ||||||||||||||||| ||eng d |
| 020 | |
▼a 9781687905376 |
| 035 | |
▼a (MiAaPQ)AAI22617460 |
| 040 | |
▼a MiAaPQ
▼c MiAaPQ
▼d 247004 |
| 082 | 0 |
▼a 540 |
| 100 | 1 |
▼a Ward, Sarah A. |
| 245 | 10 |
▼a Progress towards the Total Synthesis of Leiodelide A. |
| 260 | |
▼a [S.l.]:
▼b Indiana University.,
▼c 2019. |
| 260 | 1 |
▼a Ann Arbor:
▼b ProQuest Dissertations & Theses,
▼c 2019. |
| 300 | |
▼a 243 p. |
| 500 | |
▼a Source: Dissertations Abstracts International, Volume: 81-05, Section: B. |
| 500 | |
▼a Advisor: Williams, David R. |
| 502 | 1 |
▼a Thesis (Ph.D.)--Indiana University, 2019. |
| 506 | |
▼a This item must not be sold to any third party vendors. |
| 520 | |
▼a 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. |
| 590 | |
▼a School code: 0093. |
| 650 | 4 |
▼a Organic chemistry. |
| 650 | 4 |
▼a Chemistry. |
| 690 | |
▼a 0490 |
| 690 | |
▼a 0485 |
| 710 | 20 |
▼a Indiana University.
▼b Chemistry. |
| 773 | 0 |
▼t Dissertations Abstracts International
▼g 81-05B. |
| 773 | |
▼t Dissertation Abstract International |
| 790 | |
▼a 0093 |
| 791 | |
▼a Ph.D. |
| 792 | |
▼a 2019 |
| 793 | |
▼a English |
| 856 | 40 |
▼u http://www.riss.kr/pdu/ddodLink.do?id=T15493466
▼n KERIS
▼z 이 자료의 원문은 한국교육학술정보원에서 제공합니다. |
| 980 | |
▼a 202002
▼f 2020 |
| 990 | |
▼a ***1008102 |
| 991 | |
▼a E-BOOK |