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A Concise Total Synthesis of (-)-Mesembrine.
Lu-Ning Wang1, Qi Cui1, Zhi-Xiang Yu1
1Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University , Beijing 100871, China.
The Journal of Organic Chemistry
|October 12, 2016
Summary
A new four-step synthesis of mesembrine was developed using Rh(I)-catalyzed cycloaddition and Pd-catalyzed coupling. This efficient method provides access to mesembrine both racemically and asymmetrically.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Mesembrine is a naturally occurring alkaloid with potential pharmacological applications.
- Existing synthetic routes to mesembrine can be lengthy and complex.
- Developing efficient and stereoselective synthetic strategies is crucial for accessing mesembrine and its analogs.
Purpose of the Study:
- To achieve a concise total synthesis of mesembrine.
- To develop both racemic and asymmetric synthetic routes.
- To utilize novel catalytic reactions for key bond formations.
Main Methods:
- Rh(I)-catalyzed [5 + 1] cycloaddition of vinylcyclopropane and carbon monoxide.
- Buchwald's Palladium-catalyzed coupling of a β,γ-cyclohexenone with an aryl bromide.
- Aza-Michael addition for the final ring closure to form mesembrine.
Main Results:
- A four-step total synthesis of mesembrine was successfully accomplished.
- Both racemic and asymmetric syntheses were achieved.
- The synthesis employed a Rh(I)-catalyzed cycloaddition and a Pd-catalyzed coupling as key steps.
Conclusions:
- The developed synthetic route is concise and efficient for producing mesembrine.
- The methodology allows for stereoselective synthesis, crucial for potential pharmaceutical development.
- This work provides a valuable new approach to mesembrine synthesis.