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Synfacts 2024; 20(01): 0001
DOI: 10.1055/s-0043-1772887
DOI: 10.1055/s-0043-1772887
Synthesis of Natural Products
Synthesis of (–)-Artatrovirenol A
Lavernhe R,
Domke P,
Wang Q,
Zhu J.
*
École Polytechnique Fédérale de Lausanne, Switzerland
Enantioselective Total Synthesis of (–)-Artatrovirenol A.
J. Am. Chem. Soc. 2023;
145: 24408-14415
DOI: 10.1021/jacs.3c09683.
Enantioselective Total Synthesis of (–)-Artatrovirenol A.
J. Am. Chem. Soc. 2023;
145: 24408-14415
DOI: 10.1021/jacs.3c09683.
Key words
(–)-artatrovirenol A - sesquiterpenoid - Mukaiyama–Michael reaction - De Mayo reaction - Chugaev elimination
Significance
Zhu and co-workers report the enantioselective total synthesis of the structurally unprecedented, caged sesquiterpenoid (–)‑artatrovirenol A. Key to their approach is an intramolecular De Mayo cycloaddition/retro‑aldol sequence.
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Comment
Epoxidation of enone F to epoxide G enabled the subsequent intramolecular De Mayo reaction, leading to cycloaddition product H under UV irradiation. Deprotection initiated a retro-aldol reaction to form bromohydrin I, which was then closed to key epoxide J upon treatment with DBU.
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Publication History
Article published online:
08 December 2023
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