Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 12, Pages 8149-8156Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01051
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Funding
- National Research Foundation of Korea (NRF) - Korean Government [NRF-2018R1D1A1A02086110, NRF-2020M2A8A4027369, NRF-2014-011165]
- NRF-2018-Fostering Core Leaders of the Future Basic Science Program/Global Ph.D. Fellowship Program - Korean Government
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The total synthesis of iheyamine A from readily available ethyl 2-aminocinnamate and 5-methoxyindole-2-carboxaldehyde is described. The cyanide-catalyzed imino-Stetter reaction of an aldimine derived from ethyl 2-aminocinnamate and 5-methoxyindole-2-carboxaldehyde provided the desired unsymmetrical 2,2'-bisindole-3-acetic acid derivative. The subsequent introduction of an amino group at the C-3' position, followed by the formation of the azepine ring, completed the total synthesis of iheyamine A.
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