First total synthesis of β-carboline alkaloid trigonostemine G and its derivatives. Issue 1 (2nd January 2021)

• Record Type: Journal Article
• Authors: Szabó, Tímea; Dancsó, András; Volk, Balázs; Milen, Mátyás
• Is Part Of: Natural product research. Volume 35:Issue 1(2021)
• Page Start: 72
• Page End: 79
• Publication Date: 2021-01-02
• Subjects: Total synthesis -- β-carbolines -- indoles -- trigonostemine G -- natural products; Natural products -- Periodicals; Natural products -- Research -- Periodicals; Biological Factors -- Periodicals; Biological Products -- Periodicals; 547
• DOI: 10.1080/14786419.2019.1613401
• Languages: English
• ISSNs: 1478-6419

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}-1 H -indole to 1-formyl-β-carboline building blocks. GRAPHICAL ABSTRACT: