119th General Meeting of the KCS

Type Symposium
Area [SRC 심포지엄] New Trends and Developments in Organic Synthesis
Room No. 303호
Time WED 17:10-:
Code KCS5-15
Subject A Novel Synthetic Route for Indoloquinolizine Derivatives via Cyanide-Catalyzed Imino-Stetter Reaction
Authors 박은준, 천철홍*
고려대학교 화학과, Korea
Abstract Since natural products bearing an indoloquinolizine scaffold exhibit diverse pharmacological properties and unique chemical structures, these natural products have been considered important target molecules and there have been several synthetic routes to access these natural products. One of the most common methods to access the 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 developed a new method for the synthesis of 2-substituted indole-3-acetic acid derivatives from aldimines derived from 2-aminocinnamic acid derivatives and aldehydes via cyanide-catalyzed intramolecular imino-Stetter reaction. 1,2 We further extended this protocol to 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. Subsequent reduction of the carboxylic acid moiety to an alcohol followed by cyclization to provide tetrahydro-indoloquinolizines. Following reduction of the pyridinium ring with several nucleophiles afforded the expected indoloquinolizines. In this presentation, we will describe our new approach towards the preparation of indoloquinolizine scaffold. Reference 1. Lee, S. J.; Seo, H.-A.; Cheon, C.-H. Adv. Synth. Catal. 2016, 358, 1566. 2. Seo, H.-A.; Cheon, C.-H. J. Org. Chem. 2016, 81, 7917.
E-mail josua704@korea.ac.kr