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osu1053355296.pdf (2.92 MB)
ETD Abstract Container
Abstract Header
Studies toward the asymmetric total synthesis of mitomycin c
Author Info
Chen, Wei
Permalink:
http://rave.ohiolink.edu/etdc/view?acc_num=osu1053355296
Abstract Details
Year and Degree
2003, Doctor of Philosophy, Ohio State University, Chemistry.
Abstract
The mitomycins are a structurally unique class of naturally occurring compounds. Nearly all members of mitomycins family have shown broad spectrum antibiotic and potent antitumor activity against tumors resistant to other antineoplastic agents. One particular member of the family, mitomycin C, has been used clinically for cancer chemotherapy because of its broad spectrum activity against solid tumors. In this dissertation, a novel stereoselective approach to the ring system of the mitomycins is described. The synthesis was based on a convergent strategy involving a stereocontrolled addition of a phenyl silyl enol ether to a pyrroline N-acyliminium ion followed by an intramolecular palladium-catalyzed aryl triflate amination to afford the (9R*,9aR)-tetrahydropyrrolo[1,2-a]indole ring system. Based on similar strategy, an enantioselective synthesis of the fully functionalized mitosanes and mitosenes were achieved with high efficiency. An approach toward the isomitomycin system and efforts to introduce the key C9a methoxy group are also described.
Committee
Robert Coleman (Advisor)
Pages
279 p.
Subject Headings
Chemistry, Organic
Keywords
Total Synthesis
;
Mitomycins
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Citations
Chen, W. (2003).
Studies toward the asymmetric total synthesis of mitomycin c
[Doctoral dissertation, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1053355296
APA Style (7th edition)
Chen, Wei.
Studies toward the asymmetric total synthesis of mitomycin c.
2003. Ohio State University, Doctoral dissertation.
OhioLINK Electronic Theses and Dissertations Center
, http://rave.ohiolink.edu/etdc/view?acc_num=osu1053355296.
MLA Style (8th edition)
Chen, Wei. "Studies toward the asymmetric total synthesis of mitomycin c." Doctoral dissertation, Ohio State University, 2003. http://rave.ohiolink.edu/etdc/view?acc_num=osu1053355296
Chicago Manual of Style (17th edition)
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Document number:
osu1053355296
Download Count:
4,641
Copyright Info
© 2003, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.