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Synfacts 2022; 18(03): 0227
DOI: 10.1055/s-0041-1737867
Synthesis of Natural Products and Potential Drugs

Total Synthesis of (±)-Dalesconol A

Contributor(s):
Erick M. Carreira
,
Marlene Fadel
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
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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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