Beilstein J. Org. Chem.2025,21, 955–963, doi:10.3762/bjoc.21.79
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; CarexbrevicollisDC; cross-coupling reaction; trifluoroethylation; Introduction
Carexbrevicollis
gave brevicarine (2).
The sedge CarexbrevicollisDC 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 CarexbrevicollisDC [27], has also been identified in various other
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Graphical Abstract
Figure 1:
The structure of brevicolline ((S)-1) and brevicarine (2).