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Studies on Total Synthesis of (+)-Conagenin and (+)-Furanomycin and Copper(Ⅰ)-catalyzed Cascade Reactions

Author: WangHaiFei
Tutor: XuPengFei
School: Lanzhou University
Course: Organic Chemistry
Keywords: Natural product ()-Conagenin ()-Furanomycin Asymmetric Synthesis Tricyclic imine lactone 2 - pyrromethene Copper (I) catalyzed The Mannich , hydrogen ammoniator 2 - methylene dihydrofuro Alkyl oxidation reaction Regioselectivity Tandem Reaction
CLC: O621.3
Type: PhD thesis
Year: 2009
Downloads: 189
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Abstract


This thesis discusses the natural product ( ) - conagenin and ()-Furanomycin the asymmetric synthesis of the copper ( I ) - catalyzed 2 - pyrromethene ring and 2 - Synthesis of methylene- dihydrofuran ring . The Asymmetric Synthesis Chapter natural product ()-Conagenin ()-Conagenin its analogues Progress in Total Synthesis . Combined with the experience of the laboratory in the synthesis of α-amino acids , we the chiral Moban tricyclic imine lactone applied to the natural product ( ) - Conagenin the Asymmetric Synthesis of being a simple and feasible , the current route shortest program, from tricyclic imine lactone is over 4 steps with high selectivity , high yield synthesis of the desired (S) - methyl - serine methyl ester . The second chapter of the natural product ()-Furanomycin asymmetric synthesis of ()-Furanomycin its analogues Progress in Total Synthesis . After the completion of the natural product ()-Conagenin its analogues fully synthetic , we tried the synthesis of other natural products, small molecules ( ) - Furanomycin the imine lactone aldehyde reaction using chiral Moban tricyclic law design a simple and reasonable route . Z / E ratio 44:1 to give the desired cis- α , β - unsaturated aldehyde , and the high selectivity of the aldol product , laid the foundation for the completion of the ()-Furanomycin . 2 - of the Chapter III of copper ( I ) - catalyzed synthesis of the pyrromethene ring derivative . Pyrrole ring in the Synthesis of progress , and such extended reaction . We used a Mannich base and a copper ( I ) catalyzed hydrogen ammoniated tandem reaction , the development of an effective method of synthesis of 2 - a methylene group of the pyrrole ring . In addition, we carry out the reaction course a more in-depth study proposed a reasonable mechanism . Chapter of copper ( I ) - catalyzed 2 - Derivatives of methylene dihydrofuran ring . In this group using a base and copper ( I ) -catalyzed Mannich hydrogen ammoniated tandem reaction Synthesis of 2 - a methylene group of the pyrrole ring on the basis , we also successfully completed the 2 - methylene- dihydrofuran ring synthesis. Since the method is completed at room temperature by the oxidation reaction of intramolecular alkynyl alkoxy , the regioselectivity of this reaction is very good , reaction rate , and a small amount of catalyst .

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