Part I. Approaches Toward the Total Synthesis of Tyloindicine F; Part II. Palladium-Catalyzed C−H Functionalization of β-enaminones

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Issue Date
2010-02-26Author
Bi, Lei
Publisher
University of Kansas
Format
175 pages
Type
Dissertation
Degree Level
Ph.D.
Discipline
Medicinal Chemistry
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This item is protected by copyright and unless otherwise specified the copyright of this thesis/dissertation is held by the author.
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Tyloindicine F is a potent anticancer natural product first isolated from the Himalaya region of India. It demonstrated a unique profile in the NCI60 human tumor cell line anticancer drug screen. Due to its scarcity from natural sources, a total synthesis of tyloindicine F is desirable. Two attempts at the synthesis of this natural product have been conducted and are discussed. β-enaminones are a group of push-pull olefins whereas C-H functionalization/C-C coupling is a highly efficient method of constructing new carbon-carbon bonds. β-enaminones are highly polarized and their β; position is suitable for C-H functionalization by means of electropalladation. A novel methodology for the oxidative Hiyama coupling of β-enaminones has been developed and two new bifunctional activators/reoxidants have been found. Furthermore, a non-oxidative version for β-enaminone C-H functionalization and the decarboxylative coupling of β-enaminones were also investigated.
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