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Transition-metal Catalyzed Reactions of Enynes and Study Toward Synthesis of Indole Alkaloids: Minfiensine and Phalarine

Author: ZhangYongQiang
Tutor: TuYongQiang
School: Lanzhou University
Course: Organic Chemistry
Keywords: Transition metal Enyne compounds Indole alkaloids Minfiensine Phalarine
CLC: O621.36
Type: PhD thesis
Year: 2011
Downloads: 41
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Abstract


Enyne compound as an important reaction in organic synthesis block, to study the synthesis of new chemical conversion and applied to the natural product is one of the important research in organic chemistry. This subject, This thesis describes enyne a new chemical compound in the transition metal such as Au, Pd-catalyzed conversion, and by transition metal catalyzed enyne compound tandem reaction in the form of the natural product Minfiensine total synthesis, and finally introduced the work done by the author Phalarine synthesis study. Include the following five aspects: a. Discovered Au (Ⅰ) compounds as a Lewis acid-catalyzed enyne alcohol condensation reaction, a special class structure jump more than enyne compound. Using the product intramolecular Diels-Alder reaction and the thermal cyclization reaction, gives useful for organic synthesis of the thiophene [f] inden-structure compounds and multi-substituted allene compounds, and a class of multi-substituted thiophene [f] indene The compounds developed into fluorescent probes for the detection of mercury ions. . Development of a class of Au (Ⅰ) catalyzed indole protecting group control indole indole the acetylenic compounds regional selective cyclization reaction. When the protecting group is an electron donating group, obtained by reacting a class of pharmaceutical chemistry very important the substituted tetrahydro carboline compound; when the electron withdrawing group, the reaction to m-class exists in the natural product false oxidation indole structure compound provides a new approach for the synthesis of such alkaloids. More importantly, through the regulation of the indole protecting group is achieved indol C2, C3 is a nucleophilic reaction selectivity. III. The acetylenic compounds through the Pd-catalyzed ene Tsuj i-Trost / hydrogen amination / 1,3-H migration tandem reaction, the development of a synthetic multi-substituted pyrrole-effective method. The acetylenic compounds Au (Ⅰ) catalyzed indole indole enyne cyclization / imine positive ion cyclization tandem reaction as a key step in and build a the indole alkaloids Minfiensine the tetracyclic core fan-shaped skeleton, further implement the natural product in the form of total synthesis. Design series by Au (Ⅰ) the acetylenic compounds catalyzed indole enyne cyclization / Friedel-Crafts reaction as a key step synthesized the indole alkaloids Phalarine synthesis strategy and a useful attempt. This work has not been completed, to deepen our understanding of the reactivity of the indole and provide a useful inspiration the completed Phalarine synthesis.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Synthetic organic chemistry > Heavy organic synthesis or catalytic organic synthesis
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