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HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin
Published on: July 23, 2016
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Total Synthesis of Vinorine
Shiyuan Kang1, Yinxia Wu1, Min Hu1
1Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Pharmacy, Yunnan University, Kunming, 650091, P. R. China.
Organic Letters
|May 8, 2023
Summary
The total synthesis of vinorine, a complex alkaloid, was achieved using a flexible strategy. Key steps included aza-Achmatowicz rearrangement and Fischer indole annulation for constructing the core structure.
Area of Science:
- Organic Chemistry
- Total Synthesis
- Medicinal Chemistry
Background:
- Vinorine is a complex polycyclic alkaloid with a cage-like structure.
- The total synthesis of such intricate natural products presents significant challenges in organic chemistry.
- Developing flexible and efficient synthetic routes is crucial for accessing complex alkaloids and their analogs.
Purpose of the Study:
- To achieve the asymmetric total synthesis of vinorine.
- To develop a flexible synthetic approach for constructing the vinorine scaffold.
- To establish key reactions for building complex alkaloid structures.
Main Methods:
- Aza-Achmatowicz rearrangement followed by Mannich-type cyclization to form the 9-azabicyclo-[3.3.1]nonane scaffold.
- Fischer indole annulation for the synthesis of a common intermediate for sarpagine-ajamaline type alkaloids.
- Ireland-Claisen rearrangement for the construction of the C15-C20 bond.
Main Results:
- Successful asymmetric total synthesis of vinorine.
- Efficient installation of the 9-azabicyclo-[3.3.1]nonane core structure.
- High-yield Fischer indole annulation and Ireland-Claisen rearrangement achieved.
Conclusions:
- A flexible and efficient strategy for the total synthesis of vinorine has been established.
- The developed methodology provides access to a key intermediate for sarpagine-ajamaline type alkaloids.
- This synthesis showcases the utility of key rearrangements in constructing complex alkaloid frameworks.
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