Beilstein J. Org. Chem.2023,19, 918–927, doi:10.3762/bjoc.19.70
-dimethylallyltryptophan (DMAT) derivatives containing unactivated alkene moieties has been developed, providing green and efficient access to various six-, seven-, and eight-membered ring 3,4-fused tricyclic indoles. This type of cyclization, which was hitherto very difficult to comprehend in ergot biosynthesis and to
photocatalyst.
Keywords: decarboxylative cyclization; DMAT; ergot alkaloids; photoredox catalysis; radicals; Introduction
Visible-light photoredox catalysis is rapidly changing the way organic chemists approach the design and synthesis of molecules by offering new synthetic disconnection opportunities that
][64][65][66][67], we became fascinated in exploring whether photoredox catalysis could be applied for the activation of such unnatural amino acids to expedite the development of completely new synthetic pathways. In particular, 4-dimethylallyltryptophan (DMAT) is of interest for the following reasons
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Graphical Abstract
Figure 1:
(a) Transformations of DMAT to different classes of ergot alkaloids. (b) and (c) Strategies for the...
Beilstein J. Org. Chem.2021,17, 1814–1827, doi:10.3762/bjoc.17.124
with the prenylation of ʟ-tryptophan to dimethylallyltryptophan (DMAT). During several steps DMAT is converted to chanoclavine-I aldehyde, the last mutual intermediate. Branching into different pathways after this intermediate is mainly due to differences in the function of EasA, the enzyme catalysing
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Graphical Abstract
Figure 1:
Schematic overview of fungal interactions in the environment. Fungi can be found in essentially all...