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Synfacts 2022; 18(03): 0227
DOI: 10.1055/s-0041-1737867
DOI: 10.1055/s-0041-1737867
Synthesis of Natural Products and Potential Drugs
Total Synthesis of (±)-Dalesconol A
Zhao P,
Guo Y,
Luan X.
*
Northwest University, Xi’an and Nankai University, Tianjin, P. R. of China
Total Synthesis of Dalesconol A by Pd(0)/Norbornene-Catalyzed Three-Fold Domino Reaction and Pd(II)-Catalyzed Trihydroxylation.
J. Am. Chem. Soc. 2021;
143: 21270-21274
DOI: 10.1021/jacs.1c12118.
Total Synthesis of Dalesconol A by Pd(0)/Norbornene-Catalyzed Three-Fold Domino Reaction and Pd(II)-Catalyzed Trihydroxylation.
J. Am. Chem. Soc. 2021;
143: 21270-21274
DOI: 10.1021/jacs.1c12118.
Key words
(±)-Dalesconol A - palladium catalysis - polycyclization - Catellani reaction - Michael addition - C–H hydroxylation
Significance
(±)-Dalesconol A was first isolated from the fungus Daldinia eschscholzii and displays significant immunosuppressive properties. The natural product features a heptacyclic, highly oxidized carbon skeleton.
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Comment
Heptacycle E was efficiently accessed via norbornene/Pd(0)-catalyzed coupling and cyclization reaction of B and C, followed by an intramolecular Michael addition. Pd(II)-catalyzed trihydroxylation of G gave triol H, which was further elaborated into (±)-dalesconol A.
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Publication History
Article published online:
16 February 2022
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