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A Strategy toward Icetexane Natural Products.
Daniel J Moon1, Mohammad Al-Amin1, Robert S Lewis1
1Department of Chemistry & Biochemistry, University of Delaware, Newark, DE 19176, United States.
European Journal of Organic Chemistry
|March 30, 2019
Summary
Researchers developed a new synthetic strategy for icetexane diterpenoids, complex natural products with diverse biological activities. This approach efficiently constructs their core 6-7-6 tricyclic structure using enolate alkylation and ring-closing metathesis.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Icetexane diterpenoids are complex polycyclic natural products.
- These compounds exhibit a range of significant biological activities.
- A general synthetic route to their core structure is lacking.
Purpose of the Study:
- To develop a general synthetic approach for constructing the 6-7-6 tricyclic core of icetexane diterpenoids.
- To establish a reliable method for accessing these biologically relevant natural products.
Main Methods:
- A two-step sequence involving enolate alkylation.
- Subsequent ring-closing metathesis reaction for cyclization.
- Utilizing these methods to build the tricyclic framework.
Main Results:
- Successful construction of the 6-7-6 tricyclic core structure.
- Demonstration of a generalizable synthetic strategy.
- Provides access to key intermediates for icetexane diterpenoid synthesis.
Conclusions:
- The reported synthetic approach is effective for building the icetexane diterpenoid core.
- This method offers a valuable tool for the synthesis of these biologically active natural products.
- Further exploration of this strategy could lead to novel analogs.
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