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| Type |
Poster Presentation |
| Area |
Organic Chemistry |
| Room No. |
Event Hall |
| Time |
4월 19일 (목요일) 11:00~12:30 |
| Code |
ORGN.P-424 |
| Subject |
A Simple Synthetic Strategy of Corynanthe Family via Intramolecular Imino-Stetter reaction and Pyridinium ring Functionalizing |
| Authors |
Cheolwoo Bae, Eunjoon Park, Cheol-Hong Cheon*
Department of Chemistry, Korea University, Korea
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| Abstract |
Among the indoloquinolizine scaffolds, the monoterpene indole alkaloid, Corynanthe covers a structure of many natural products. These natural products are very valuable because they have various pharmacological activities. One of the most common methods to access this core indoloquinolizine structure is the Pictet-Spengler reaction of imines derived from tryptamine and aldehydes. Another one is the Bischler-Napieralski reaction of 3-piperidioneindole derived from tryptamine and furancarboxylic acid. However, these methods generally require additional steps to generate another six-membered ring and toxic metals for coupling reactions.
Recently, our group reported the synthesis of indole-3-acetic acid derivatives bearing a pyridyl moiety at the 2-position from aldimines obtained from 2-aminocinnnamic acid derivatives and various pyridinecarbaldehydes via cyanide-catalyzed intramolecular imino-Stetter reaction.1 Subsequent reduction of the carboxylic acid moiety to an alcohol followed by cyclization to provide tetrahydro-indoloquinolizines. In this poster presentation, we disclose our efforts for the functionalization of the pyridinium ring with a nucleophile, to make the structure of Corynanthe. The advantage of this strategy is that this could be a general synthetic protocol toward Corynanthe family.
Reference
1. Park, E; Cheon, C.-H. Org. Biomol. Chem. 2017, 15, 10265
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| E-mail |
cwbae7@naver.com |
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121st General Meeting of the KCS