Chinese Journal of Organic Chemistry >
Recent Advances of Wagner-Meerwein Rearrangement in Natural Product Synthesis
Received date: 2024-08-07
Revised date: 2024-09-10
Online published: 2024-10-29
Supported by
National Natural Science Foundation of China(22188101); National Natural Science Foundation of China(22222105); National Natural Science Foundation of China(22301146); National Natural Science Foundation of China(22371142); Frontiers Science Center for New Organic Matter, Nankai University(63181206); Fundamental Research Funds for the Central Universities(23JCYBJC01410); China Postdoctoral Science Foundation(332608)
The Wagner-Meerwein rearrangement reaction, renowned for its unique capability in efficiently constructing quaternary chiral centers and achieving carbon skeleton rearrangement within molecules, has been widely applied in the synthesis of numerous complex molecules since its discovery. By incorporating rational biosynthetic pathway analyses, the Wagner- Meerwein rearrangement can be ingeniously introduced into synthetic design to rapidly and efficiently construct ring systems that are challenging to achieve through conventional methods, particularly polycyclic natural products with multiple contiguous quaternary carbon stereocenters. In recent years, the application of the Wagner-Meerwein rearrangement in the synthesis of terpenoids and steroids has increased significantly, demonstrating its unique synthetic advantages. The latest applications of the Wagner-Meerwein rearrangement in the synthesis of these complex natural products since 2019 are primarily summarized, highlighting its distinct advantages in constructing ring systems with quaternary carbon chiral centers.
Key words： Wagner-Meerwein rearrangement; natural product; total synthesis; terpenoid; steroid
Jie Chen , Jun Li , Xianwen Long , Haixiang Shen , Jun Deng . Recent Advances of Wagner-Meerwein Rearrangement in Natural Product Synthesis[J]. Chinese Journal of Organic Chemistry, 2025 , 45(3) : 896 -912 . DOI: 10.6023/cjoc202408010
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