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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-420 |
| Subject |
Development of General Synthetic Route of Phenanthroindolizidine Alkaloids via Iterative Suzuki-Miyaura Coupling by Three-Column Operations |
| Authors |
Young-In Jo, Cheol-Hong Cheon*
Department of Chemistry, Korea University, Korea
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| Abstract |
Since the phenanthroindolizidine alkaloids display various interesting biological activities, these alkaloids have received increasing attention in past decades. As a result, numerous synthetic pathways to access these natural products have been developed. However, most of the approaches have focused on the synthesis of each specific target molecule through an independent synthetic pathway. Furthermore, the previous syntheses generally required relatively lengthy synthetic sequences. For this reason, it is important to develop a efficient and general synthetic pathway toward phenanthroindolizidine alkaloids. To address this problem, we attempted to develop general synthetic routes for several phenanthroindolizidine alkaloids from readily available starting materials.
Recently, our research group developed a highly efficient method for the preparation of 3-brormo-4-alkoxyphenyl boronic acid N-methyliminodiacetic acid (MIDA) ester, and synthesized meta-terphenyl natural products using the resulting MIDA boronates as key building blocks in iterative Suzuki-Miyaura reaction.1 Based on this result, we further attempted to develop the total syntheses of phenanthroindolizidine alkaloids via iterative Suzuki-Miyaura reaction using MIDA boronates as key building blocks. This approach allowed us to finish the total synthesis of these natural products in only three column operations.
Reference
1. Lee, C.-Y.; Cheon, C.-H. Adv. Synth. Catal. 2017, 359, 3831.
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| E-mail |
jyisky5@naver.com |
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121st General Meeting of the KCS