期刊
ORGANIC CHEMISTRY FRONTIERS
卷 10, 期 1, 页码 68-73出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01460b
关键词
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资金
- National Natural Science Foundation of China [22101290, 21572180]
- Intergovernmental Science and Technology Cooperation and Exchange Program between P. R. China and Romania [43-24-20180510]
- Chinese Academy of Sciences
- Shanghai Institute of Materia Medica
Here, we present a unified strategy for the divergent total synthesis of six Elaeocarpus alkaloids in 6-10 steps from commercially available materials. This strategy involves the rapid construction of the tetrahydrobenzopyran-4-one framework through a series of reactions, including aldol/dehydration/oxa-Michael processes. Additionally, a key NbCl5-mediated intramolecular Mannich reaction is utilized to build the C ring and ensure the presence of both stereoisomers found in the natural products. Furthermore, a diversification step is achieved through the intermediacy of thioamide.
Herein we report a unified strategy for the divergent total synthesis of six Elaeocarpus alkaloids in 6-10 steps from commercially available materials. This modular approach relied on the rapid construction of the tetrahydrobenzopyran-4-one framework through an aldol/dehydration/oxa-Michael process to set all carbons and functional groups ready for the core construction. A key NbCl5-mediated intramolecular Mannich reaction was used to build the C ring and secure both stereoisomers existing in these natural products. Finally, a diversification was achieved through the intermediacy of thioamide, with the side chain of elaeocarfoline A/B installed by an Eschenmoser sulfide contraction/reduction sequence.
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