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Studies on the syntheses of β-carboline alkaloids brevicarine and brevicolline

  • Benedek Batizi,
  • Patrik Pollák,
  • András Dancsó,
  • Péter Keglevich,
  • Gyula Simig,
  • Balázs Volk and
  • Mátyás Milen

Beilstein J. Org. Chem. 2025, 21, 955–963, doi:10.3762/bjoc.21.79

Graphical Abstract
  • reactions: reduction of ring A of the β-carboline skeleton or trifluoroethylation of the pyrrole moiety occurred, leading to interesting and potentially useful derivatives. Keywords: alkaloid; β-carboline; Carex brevicollis DC; cross-coupling reaction; trifluoroethylation; Introduction Carex brevicollis
  • gave brevicarine (2). The sedge Carex brevicollis DC has long been recognized for its ability to stimulate the contraction of smooth muscles [2]. This effect may be linked to the oxytocic activity of (S)-brevicolline ((S)-1), which has been studied on pregnant mammals [24][25]. (S)-Brevicolline, first
  • brevicarine (2) from (S)-brevicolline ((S)-1) (see Scheme 2) and their biogenetic relationship suggest that (S)-brevicolline could serve as a biosynthetic intermediate of brevicarine (2) in plants [19]. Brevicarine (2), isolated in 1967 from Carex brevicollis DC [27], has also been identified in various other
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Published 20 May 2025
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