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- W2884763977 abstract "Nitrogen-containing compounds have a great interest as this element is found in natural products and drugs, thus the development of efficient methods for their preparation is highly desirable. First, a stereodivergent and enantioselective method has been developed for the total syntheses of chaetominine-type alkaloids including the proposed structures of (-)-pseudofischerine, (-)-aniquinazoline D and (-)-isochaetominine, (-)-isochaetominines A–C, (+)-14-epi-isochaetominine C, as well as the four hitherto unknown stereoisomers of isochaetominine C. The structures of natural (-)-pseudofischerine and (-)-aniquinazoline D have been revised as (-)-isochaetominine C and the structure of the natural (-)-isochaetominine have been revised to (-)-11-epi-chaetominine based on our synthetic efforts. Next, an azaphilic radical cascade cyclization reaction has been developed leading to the efficient synthesis of imidazo-fused heteroaromatics from easily available N-heteroaryl-O-propargyl carbamates. The organocatalyzed electrochemical synthesis has a broad scope, tolerates many common functional groups, and proceeds under mild conditions without the need of transition-metal catalysis or chemical oxidant. Finally, two approaches toward analogs of the CHOI unit have been developed. The key steps of the synthetic route were based on Pd-catalyzed C-allylation and N-allylation, which converted a cyclic bis-allylic substrate into a hexahydroindole scaffold. Depending on the strategy applied, the position of alkene moiety of the resulting hexahydroindole can be obtained at different positions. One-carbon homologation followed by epoxidation or syn-dihydroxylation of the resulting bicyclic intermediates afforded the desired CHOI analogues." @default.
- W2884763977 created "2018-08-03" @default.
- W2884763977 creator A5050322737 @default.
- W2884763977 date "2017-07-12" @default.
- W2884763977 modified "2023-09-27" @default.
- W2884763977 title "Stereodivergent and enantioselective total syntheses of chaetominine-type alkaloids and azaphilic radical cascade cyclization for the synthesis of imidazo-fused heteroaromatics and toward analogs of the 2-Carboxyl-6-HydroxyOctahydroIndole (CHOI) Unit" @default.
- W2884763977 hasPublicationYear "2017" @default.
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