The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Scalable Total Syntheses of N-Linked Tryptamine Dimers by Direct Indole−Aniline Coupling: Psychotrimine and Kapakahines B and F
Open accessAbstract
This report details the invention of a method to enable syntheses of psychotrimine (1) and the kapakahines F and B (2, 3) on a gram scale and in a minimum number of steps. Mechanistic inquiries are presented for the key enabling quaternization of indole at the C3 position by electrophilic attack of an activated aniline species. Excellent chemo-, regio-, and diastereoselectivities are observed for reactions with o-iodoaniline, an indole cation equivalent. Additionally, the scope of this reaction is broad with respect to the tryptamine and aniline components. The anti-cancer profiles of 1-3 have also been evaluated.
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Small molecule blockade of transcriptional coactivation of the hypoxia-inducible factor pathway
Kung, A. L., Zabludoff, S. D., France, D. S., Freedman, S. J., Tanner, E. A., Vieira, A., Cornell-Kennon, S., Lee, J., Wang, B., Wang, J., et al. (2004) · Cancer Cell · doi:10.1016/j.ccr.2004.06.009 · Cited by 480
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Aiming for the Ideal Synthesis
Gaich, T., & Baran, P. S. (2010) · The Journal of Organic Chemistry · doi:10.1021/jo1006812 · Cited by 647
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Metadata
- Authors
- Newhouse, T., Lewis, C. A., Eastman, K. J., & Baran, P. S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-04-28
- Volume
- 132
- Issue
- 20
- Pages
- 7119-7137
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2162328172
- Cited by
- 187
- References
- 1
- FWCI
- 9.47
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: Scalable Total Syntheses of N-Linked Tryptamine Dimers by Direct Indole−Aniline Coupling: Psychotrimine and Kapakahines B and F. https://app.cochat.ai/papers/10.1021/ja1009458
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- Newhouse, T., Lewis, C. A., Eastman, K. J., & Baran, P. S. (2010). Scalable Total Syntheses of N-Linked Tryptamine Dimers by Direct Indole−Aniline Coupling: Psychotrimine and Kapakahines B and F. Journal of the American Chemical Society. https://doi.org/10.1021/ja1009458
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
