Total Synthesis of the <i>Melodinus</i> Alkaloid (±)-Melohemsine K
The first total synthesis of the novel <i>Melodinus</i> alkaloid melohemsine K is described in five steps from known precursors. The key reaction of the synthesis is a tandem enamine formation/retro-aza-Michael reaction/Diels-Alder cycloaddition/intramolecular lactamization reaction cascade between indole-fused azepine and aldehyde precursors, forging the critical CDE tricyclic system. The synthesis provided a general approach to novel <i>Melodinus</i> alkaloids.
Authors
- Xingang Xie (ORCID: https://orcid.org/0000-0002-0707-1229)
- Shanhao Lin
- Huanwang Jing (ORCID: https://orcid.org/0000-0003-3814-0087)
- Gaoyuan Zhao (ORCID: https://orcid.org/0000-0003-4838-865X)
- Jinbo Duan
- Huilin Li (ORCID: https://orcid.org/0000-0001-8088-6718)
- Jing Fang
- Xuegong She (ORCID: https://orcid.org/0000-0002-3002-2433)
Institutions
- Lanzhou University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-25
- DOI
- https://doi.org/10.1021/acs.joc.5c00545
- Citations
- 2
- Primary Topic
- Alkaloids: synthesis and pharmacology
- Type
- article
- Field-Weighted Citation Impact
- 3.11
Funders
- National Natural Science Foundation of China
- Science and Technology Department of Gansu Province