Based On Actiation Of The C-H Bond Functionalization Method To Synthesis Fragments Of (-)-tetrazomine And (+)-deoxoproxopinine

In recent years, functionalizing traditionally inert carbon–hydrogen bonds represents apowerful transformation in organic synthesis, providing new entries to valuable structuralmotifs and improving the overall synthetic efficiency. The first chapter simply reviews the Pd–catalyzed C-H bond functionaliztion history and the current status of the development. Liststhe activation of Pd catalyzed C-H bond formation of C-C, C-O bonds and syntheticapplication. The chapter two summary the history of synthesis nature products containpiperidine ting. Leading to the conclusion: Using Pd-catalyzed Direct Functionalization ofcarbon–hydrogen bonds activation to building natural products of the molecular skeletoncontaining piperidine ring, can greatly improve the efficiency of synthesis and can be wellcontrolled chirality. We chosen the nature Alanine as start material. Connect8–aminoquinoline as direct group. First, A palladium-catalyzed alkylation of primary C(sp3)–Hbonds with alkyl iodides for the synthesis of optically active unnatural a-amino acidsderivatives is described. Then，palladium-catalyzed Acetoxylation of secondary C(sp3)–Hbonds for the synthesis of optically active unnatural β-Hydroxy α-amino acids derivatives isdescribed。Removal the direct group to build molecular skeleton. The chapter three details themethods to remove direct group. Finally we find Lewis acids BF3.Et2O and tertiary amide thatTransformed by secondary amide using DMAP and (Boc)2O alkaline hydrolysis by LiOH andhydrogen peroxide can be efficiently removed8–aminoquinoline. The chapter fourIntroducing the methods to synthesis the two nature products of (-)-tetrazomine and(+)-deoxoproxopinine using palladium-catalyzed arylation、alkylation and Acetoxylation. Wehave try many methods of palladium-catalyzed carbon–hydrogen bonds activation to buildAryl fragment Included in the (-)-tetrazomine and two route to synthesis(+)-deoxoproxopinine. We completed the core skeleton of both two products. Theexperimental section, full characterization data for all products, cited references, some copiesof seleced original spectra are found at the end of this paper.