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From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028
Published on: January 13, 2017
Total synthesis of (+)-acutiphycin
Ryan M Moslin1, Timothy F Jamison
1Massachusetts Institute of Technology, Department of Chemistry, Cambridge, Massachusetts 02139, USA.
The Journal of Organic Chemistry
|November 8, 2007
Summary
Researchers discovered novel nickel-catalyzed reactions for synthesizing complex molecules. A highly convergent total synthesis of (+)-acutiphycin was achieved, showcasing advanced organic synthesis strategies.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Catalysis
Background:
- Total synthesis of natural products drives innovation in synthetic methodology.
- Developing efficient and regioselective reactions is crucial for complex molecule construction.
Purpose of the Study:
- To achieve the total synthesis of (+)-acutiphycin.
- To discover new synthetic methodologies, specifically catalytic reactions.
Main Methods:
- Exploration of nickel-catalyzed reductive coupling reactions between aldehydes and 1,6-enynes.
- Development of a convergent synthetic route employing SmI2-mediated Reformatsky coupling and macrolactonization.
- Utilized retro-ene reaction of an alkoxyalkyne for macrolactonization initiation.
Main Results:
- Discovery of additive-free, highly regioselective nickel-catalyzed coupling of aldehydes and 1,6-enynes.
- Construction of an advanced intermediate towards (+)-acutiphycin.
- Successful and highly convergent total synthesis of (+)-acutiphycin in 18 steps.
Conclusions:
- The developed nickel-catalyzed reaction offers a new tool for organic synthesis.
- The total synthesis of (+)-acutiphycin demonstrates the power of convergent strategies and specific coupling reactions.
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