Skeletal diversification by C-C cleavage to access bicyclic frameworks from a common tricyclooctane intermediate
Ian Bakanas1, Jess C Tang1, Richmond Sarpong1
1Department of Chemistry, University of California-Berkeley, Berkeley, California, USA. rsarpong@berkeley.edu.
Chemical Communications (Cambridge, England)
|March 14, 2023
Summary
This study details a two-step method for creating strained tricyclooctane compounds using blue light. Subsequent scaffold cleavage selectively yields diverse bicyclic structures, aiding complex molecule synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Photochemistry
Background:
- Tricyclo[3.2.1.03,6]octane scaffolds are valuable synthetic intermediates.
- Efficient methods for diversifying these strained systems are needed.
- Controlled C-C bond cleavage is crucial for accessing complex molecular architectures.
Purpose of the Study:
- To develop a facile synthetic route to tricyclo[3.2.1.03,6]octanes.
- To explore selective C-C bond cleavage strategies for these strained scaffolds.
- To synthesize diverse bicyclic cores from tricyclooctane precursors.
Main Methods:
- Two-step synthesis involving blue light-mediated [2+2] cycloaddition.
- Exploration of various C-C cleavage reactions.
- Selective synthesis of bicyclo[3.1.1]heptane, bicyclo[3.2.1]octane, and bicyclo[3.2.0]heptane.
Main Results:
- Successful preparation of strained tricyclooctane intermediates.
- Demonstration of selective C-C bond cleavage pathways.
- Access to diverse bicyclic frameworks including bicyclo[3.1.1]heptane, bicyclo[3.2.1]octane, and bicyclo[3.2.0]heptane.
Conclusions:
- A novel and efficient method for tricyclooctane synthesis and diversification is presented.
- The findings provide a foundation for utilizing C-C cleavage in strained frameworks for complex synthesis.
- This work expands the synthetic utility of bicyclic scaffolds in organic chemistry.
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