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The [5+5] route to the phenanthrene skeleton.
James W Herndon1, Bishnu Dhakal1
1Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, New Mexico, 88003, USA.
ARKIVOC : Free Online Journal of Organic Chemistry
|March 14, 2017
Summary
This study details the net [5+5] cycloaddition reaction between unsaturated Fischer carbene complexes and alkynylbenzaldehydes. This efficient synthesis directly yields medicinally relevant hydrophenanthrene ring systems.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Catalysis
Background:
- Fischer carbene complexes are versatile organometallic reagents.
- Hydrophenanthrene scaffolds are present in numerous natural products with biological activity.
- Efficient synthetic routes to complex polycyclic systems are highly sought after.
Purpose of the Study:
- To describe the historical development of a novel cycloaddition reaction.
- To highlight the utility of this reaction in synthesizing hydrophenanthrene ring systems.
- To showcase applications in natural product synthesis.
Main Methods:
- Coupling of γ,δ-unsaturated Fischer carbene complexes with *o*-alkynylbenzaldehydes.
- Utilizing a net [5+5] cycloaddition strategy.
- Exploring the reaction's scope and application in synthesizing complex molecules.
Main Results:
- Direct formation of bicyclo[4.4.0]decane ring systems.
- Each reactant contributes five carbons to the newly formed ring.
- Successful synthesis of medicinally important natural product parent ring systems.
Conclusions:
- The net [5+5] cycloaddition is an effective method for constructing hydrophenanthrenes.
- This reaction provides a streamlined approach to valuable chemical scaffolds.
- The methodology holds significant potential for drug discovery and development.