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Total synthesis of (±)-isophellibiline.
Raymond L Funk1, Johannes Belmar
1Department of Chemistry, Pennsylvania State University, University Park, PA 16802, USA.
Tetrahedron Letters
|February 7, 2012
Summary
The total synthesis of (±)-isophellibiline, a nonaromatic homoerythrinan alkaloid, was achieved. This study presents the first successful synthesis of this complex natural product family.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- The homoerythrinan alkaloid family is a class of nonaromatic natural products.
- Isophellibiline is a member of this alkaloid family.
- Total synthesis provides access to complex natural products for further study.
Purpose of the Study:
- To describe the first total synthesis of (±)-isophellibiline.
- To establish a synthetic route for nonaromatic homoerythrinan alkaloids.
- To demonstrate the utility of specific synthetic strategies for complex tetracyclic systems.
Main Methods:
- Utilized a retrocycloaddition/cycloaddition reaction of an amidodioxin.
- Employed an intramolecular Heck reaction for ring construction.
- Incorporated a 6π-electrocyclic ring closure of a dienoic acid.
Main Results:
- Successfully synthesized (±)-isophellibiline.
- Assembled the tetracyclic ring system of the natural product efficiently.
- Demonstrated a viable strategy for accessing nonaromatic homoerythrinan alkaloids.
Conclusions:
- The total synthesis of (±)-isophellibiline was accomplished.
- The developed strategy is effective for constructing the homoerythrinan skeleton.
- This work opens avenues for the synthesis of related alkaloids.
