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Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
Published on: November 30, 2020
First total synthesis of (-)-sinularianin B
Koichiro Ota1, Hiroaki Miyaoka
1School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Chemical Communications (Cambridge, England)
|July 24, 2013
Summary
Researchers achieved the first enantioselective total synthesis of (-)-sinularianin B, a unique sesquiterpenoid from soft coral. This 16-step synthesis utilized a key tandem alkylation for cyclopentane formation.
Area of Science:
- Organic chemistry
- Natural product synthesis
- Marine natural products
Background:
- (-)-Sinularianin B is a structurally unique sesquiterpenoid.
- This compound was isolated from the Formosan soft coral Sinularia sp.
Purpose of the Study:
- To achieve the first enantioselective total synthesis of (-)-sinularianin B.
- To explore novel synthetic strategies for complex natural products.
Main Methods:
- A 16-step synthetic route was designed and executed.
- Key transformations included a tandem intermolecular-intramolecular alkylation.
- A 5-endo cyclization was employed for cyclopentane ring formation with a tertiary hydroxy group.
Main Results:
- The enantioselective total synthesis of (-)-sinularianin B was successfully accomplished.
- The overall yield of the synthesis was 39.5% over 16 steps.
- The synthesis established a robust method for constructing the core structure.
Conclusions:
- The first enantioselective total synthesis of (-)-sinularianin B provides access to this unique marine natural product.
- The developed synthetic methodology, particularly the tandem alkylation and cyclization, can be applied to other complex sesquiterpenoids.
- This work contributes to the field of natural product synthesis and medicinal chemistry exploration.
