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Total Synthesis of Principinol B
Qiang Du1, Zhibo Fan1, Ming Yang1
1State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, Gansu Province, 730000, China.
Angewandte Chemie (International Ed. in English)
|February 23, 2024
Summary
We report the first asymmetric total synthesis of principinol B, a complex grayanoid. This achievement involved constructing its unique oxabicyclo[3.2.1] architecture using advanced synthetic organic chemistry methods.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Principinol B is a grayanoid with a complex oxabicyclo[3.2.1] architecture.
- Grayanoids are natural products with potential biological activities.
Purpose of the Study:
- To achieve the first asymmetric total synthesis of principinol B.
- To develop a synthetic strategy for constructing the oxabicyclo[3.2.1] core structure.
Main Methods:
- Convergent synthesis of a functionalized 5/7/6/5 tetracyclic intermediate.
- Diastereoselective intermolecular aldol reaction to couple two enantiomerically enriched fragments.
- Carbonyl-olefin metathesis and Williamson ether synthesis to build the oxabicyclo[3.2.1] architecture.
Main Results:
- Successful asymmetric total synthesis of principinol B.
- Construction of the challenging oxabicyclo[3.2.1] core structure with a 6,10-ether bridge.
- Demonstration of efficient coupling and cyclization strategies.
Conclusions:
- The developed synthetic route provides access to principinol B.
- The methodology can be applicable to the synthesis of other complex grayanoids.
- This work expands the toolkit for constructing intricate polycyclic natural products.
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