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Total Synthesis of (-)-Mucocin
Stefan Bäurle1, Sabine Hoppen1, Ulrich Koert1
1Institut für Chemie der Humboldt-Universität, Hessische Strasse 1-2, D-10115 Berlin (Germany), Fax: (+49) 30-2093-7266.
Angewandte Chemie (International Ed. in English)
|May 2, 2018
Summary
Researchers developed a modular synthesis for annonaceous acetogenin (-)-mucocin. Key steps include endo-selective tetrahydropyran ring formation and stable butenolide coupling for this complex natural product.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Annonaceous acetogenins are a class of polyketide natural products with potent biological activities.
- (-)-Mucocin is a significant member of this class, presenting a complex structural challenge for synthesis.
Purpose of the Study:
- To report a highly convergent and modular strategy for the total synthesis of (-)-mucocin.
- To highlight novel methodologies for constructing key structural motifs.
Main Methods:
- Employing a modular approach for efficient assembly of the carbon skeleton.
- Utilizing an endo-selective epoxide opening for tetrahydropyran ring construction.
- Investigating the stability of the butenolide moiety during organometallic coupling.
Main Results:
- Successful total synthesis of (-)-mucocin was achieved.
- Demonstrated efficient and stereoselective formation of the tetrahydropyran ring.
- Confirmed the stability of the butenolide under coupling conditions.
Conclusions:
- The developed strategy offers a robust and versatile route to (-)-mucocin.
- The synthetic methodology is applicable to other complex acetogenins.
- This work advances the field of natural product synthesis.
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