Total synthesis of (+/-)-actinophyllic acid
Connor L Martin1, Larry E Overman, Jason M Rohde
1Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
Journal of the American Chemical Society
|May 22, 2008
Summary
Researchers report the first total synthesis of actinophyllic acid. Key steps involved oxidative coupling and an aza-Cope-Mannich rearrangement to construct the natural product
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Actinophyllic acid is a complex natural product with a unique ring system.
- Previous synthetic routes to actinophyllic acid were lacking.
Purpose of the Study:
- To achieve the first total synthesis of (+/-)-actinophyllic acid.
- To develop an efficient and concise synthetic strategy.
Main Methods:
- Utilized an intramolecular oxidative coupling of ketone and malonic ester enolates.
- Employed an aza-Cope-Mannich rearrangement to assemble the core structure.
- Synthesized the target molecule from di-tert-butyl malonate.
Main Results:
- Successfully completed the first total synthesis of (+/-)-actinophyllic acid.
- Achieved an 8% overall yield.
- The synthesis involved a concise sequence with only seven isolated intermediates.
Conclusions:
- The developed synthetic route provides access to actinophyllic acid.
- The key reactions, oxidative coupling and aza-Cope-Mannich rearrangement, are effective for constructing the natural product's complex architecture.
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