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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-423 |
| Subject |
Total Synthesis of Goniomitine via Intramolecular Imino-Stetter Reaction |
| Authors |
Eunjoon Park, Sungjun SHIM, Cheol-Hong Cheon*
Department of Chemistry, Korea University, Korea
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| Abstract |
Goniomitine, isolated from the root bark of Gonioma Malagasy, has significant biological activity such as antiproliferative activity in several tumor cell lines. In addition to its biological activity, the unique structure of this natural product, which is aminal-containing tetracyclic core, is differentiated from other Aspidosperma alkaloids. This critical biological activity, coupled with the intriguing structure of the goniomitine, sparked interest within the synthetic community. Although there have been six reported total syntheses of (±)-goniomitine, as well as five asymmetric total syntheses, we still felt that the development of more efficient synthesis methods for this natural product to further evaluate its biological activity.
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] With this result in hand, all carbon skeletons of the target natural product could be introduced in the first imino-Stetter reaction of aldmine derived from 2-aminocinnamic acid derivative and α,β-unsaturated ketones. The desired natural product can be synthesized by appropriate transformation of the resulting indole product leading to the completion of the total synthesis in very short steps. In this poster presentation, we will describe our endeavors toward goniometine.
Reference
[1] Cheon, C.-H. et al. Adv. Synth. Catal. 2016, 358, 1566.
[2] Cheon, C.-H. et al. J. Org. Chem. 2016, 81, 7917.
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| E-mail |
josua704@korea.ac.kr |
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121st General Meeting of the KCS