Journal
SYNTHESIS-STUTTGART
Volume 49, Issue 18, Pages 4141-4150Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588438
Keywords
Pictet-Spengler reaction; indole alkaloids; azepinoindoles; biomimetic synthesis; cyclizations; stereoselectivities
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Funding
- Japan Society for the Promotion of Science (JSPS) [16K18849]
- Grants-in-Aid for Scientific Research [16K18849] Funding Source: KAKEN
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The hyrtiazepine alkaloids are a family of bisindole natural products that have the azepinoindole backbone. We developed a biomimetic approach by constructing the azepinoindole core in a one-pot manner through 1,4-diazabicyclo[2.2.2]octane/2,2,2-trifluoroethanol (DABCO/TFE) promoted Pictet-Spengler reaction onto the C-4 position of tryptophan. This strategy allowed the synthesis of common key structures of these families. The key intermediate can be converted into the 3H-pyrano[2,3-b:5,6-e']diindol intermediate present in hyrtimomines A and B, as well as the azepinoindole core present in fargesine.
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