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Updated: May 23, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Concise total synthesis of (-)-mersicarpine.
Yusuke Iwama1, Kentaro Okano, Kenji Sugimoto
1Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
A concise total synthesis of (-)-mersicarpine was achieved from a readily available cyclohexanone precursor. The key azepinoindole core was efficiently constructed using a DIBAL-H-mediated reductive ring-expansion of an oxime.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- (-)-Mersicarpine is a complex alkaloid with potential biological activities.
- Efficient synthetic routes are crucial for accessing and studying such natural products.
Purpose of the Study:
- To develop a concise and efficient total synthesis of (-)-mersicarpine.
- To establish a novel method for constructing the azepinoindole core.
Main Methods:
- The synthesis commenced from a known cyclohexanone derivative.
- A key step involved a DIBAL-H-mediated reductive ring-expansion of an oxime to form the azepinoindole core.
Main Results:
- A concise total synthesis of (-)-mersicarpine was successfully accomplished.
- The DIBAL-H-mediated reaction proved effective for constructing the target core structure.
Conclusions:
- This study presents an efficient and practical route to (-)-mersicarpine.
- The developed methodology offers a valuable approach for synthesizing related azepinoindole compounds.
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