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First total synthesis of β-carboline alkaloid trigonostemine G and its derivatives

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Abstract The β-carboline core is the base structure of several biologically active natural and unnatural compounds. Herein, we report the first total synthesis of trigonostemine G, which is a newly… Click to show full abstract

Abstract The β-carboline core is the base structure of several biologically active natural and unnatural compounds. Herein, we report the first total synthesis of trigonostemine G, which is a newly isolated natural β-carboline alkaloid from the twigs of Trigonostemon filipes. Synthesis of two structurally close derivatives of trigonostemine G is also reported. Key step of the syntheses involves a nucleophilic addition of 5-{[tert-butyl(dimethyl) silyl]oxy}-1H-indole to 1-formyl-β-carboline building blocks. GRAPHICAL ABSTRACT

Keywords: trigonostemine; first total; total synthesis; carboline; carboline alkaloid

Journal Title: Natural Product Research
Year Published: 2019

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