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020 ▼a 9780438173040
035 ▼a (MiAaPQ)AAI10837881
035 ▼a (MiAaPQ)ucla:17133
040 ▼a MiAaPQ ▼c MiAaPQ ▼d 247004
0820 ▼a 547
1001 ▼a Allred, Tyler Keith.
24510 ▼a Synthetic Studies on the Marineosins and Other Related Complex Prodiginines.
260 ▼a [S.l.]: ▼b University of California, Los Angeles., ▼c 2018.
260 1 ▼a Ann Arbor: ▼b ProQuest Dissertations & Theses, ▼c 2018.
300 ▼a 526 p.
500 ▼a Source: Dissertation Abstracts International, Volume: 79-12(E), Section: B.
500 ▼a Adviser: Patrick G. Harran.
5021 ▼a Thesis (Ph.D.)--University of California, Los Angeles, 2018.
520 ▼a Chapter One provides an overview of complex prodiginine alkaloids: streptorubin, roseophilin, and the marineosins. This includes a brief discussion of the prototypical structural features of the prodiginine class of natural products, their isola
520 ▼a We have developed a unique method of constructing the pyrrolophane core via a late stage phosphoryl-transfer mediated macroaldolization, which was utilized in the production of roseophilin. Chapter Two chronicles our efforts to adapt this approa
520 ▼a Chapter Three discusses in detail our efforts to capitalize on the electron rich nature of the prodiginine core to engage a reactive functionality on the aliphatic chain and induce macrocyclization. Initial efforts were aimed at photoinduced ele
520 ▼a Chapter Four details our efforts to utilize the reactivity discovered in model system studies, which culminated in the synthesis of marineosin A. The photoinduced rearrangement of pyridinophane N-oxides proved particularly powerful in the produc
520 ▼a The readily apparent utility of the photoinduced rearrangement methodology caused us to revisit roseophilin. Chapter Five presents how the aforementioned rearrangement allows for facile access to the roseophilin pyrrolophane, which can be readil
590 ▼a School code: 0031.
650 4 ▼a Organic chemistry.
690 ▼a 0490
71020 ▼a University of California, Los Angeles. ▼b Chemistry 0153.
7730 ▼t Dissertation Abstracts International ▼g 79-12B(E).
773 ▼t Dissertation Abstract International
790 ▼a 0031
791 ▼a Ph.D.
792 ▼a 2018
793 ▼a English
85640 ▼u http://www.riss.kr/pdu/ddodLink.do?id=T14999590 ▼n KERIS ▼z 이 자료의 원문은 한국교육학술정보원에서 제공합니다.
980 ▼a 201812 ▼f 2019
990 ▼a ***1012033