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129th General Meeting of Korean Chemical Society & Exposition Synthetic Studies towards Yohimbine Alkaloids

Submission Date :
2 / 28 / 2022 , 15 : 43 : 49
Abstract Number :
Presenting Type:
Poster Presentation
Presenting Area :
Organic Chemistry
Authors :
Jihyun Kang, Myunghoon Jeong1, Cheol-Hong Cheon1,*
Chemistry, Korea University, Korea
1Department of Chemistry, Korea University, Korea
Assigned Code :
ORGN.P-626 Assigend Code Guideline
Presenting Time :
April 15 (FRI) 11:00~13:00
Yohimbine is one of the most well-known indole alkaloids with a rich chemical and medicinal history. The first total synthesis of the racemic compound was achieved more than 50 years ago by Van Tamelen and co-workers. Since the seminal synthesis, several other syntheses including asymmetric synthesis have been reported. Most previous syntheses of yohimbine commenced with a specific starting material containing the key fragment, the ester group and the hydroxyl group at the C-16 and C-17 positions with appropriate stereochemistry, respectively. Subsequent construction of the C/D rings with tryptamine completed the synthesis of yohimbine. However, these conventional approaches required relatively lengthy synthetic sequences to control stereochemistry and to make pentacyclic structure. In this poster presentation, our endeavor towards the development of a new synthetic approach for yohimbine will be presented. The cyanide-catalyzed imino-Stetter reaction of aldimine derived from 2-aminocinnamic acid derivative and pyridine-2-carboxaldehyde bearing acetyl group at the C5-postionprovided the corresponding indole-3-acetic acid derivative. Subsequent formation of the 6-membered C-ring followed by Michael addition of the malonate at C-15 position provided a rapid access to the pentacyclic intermediate. By controlling the stereochemistry after next several steps, it is expected that synthesis of yohimbine alkaloids could be completed.