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Synfacts 2025; 21(11): 1075
DOI: 10.1055/a-2703-1422
Synthesis of Natural Products

Total Synthesis of (±)-Harziandione

Autoren

Wu J, Bao J, Deng J, Tian H, Gui J *. Shanghai Institute of Organic Chemistry, P. R. China
Concise Syntheses of Harziane Diterpenoids by Merging Local Desymmetrization and Radical Retrosynthesis.

J. Am. Chem. Soc. 2025;
147: 30599-30605
DOI: 10.1021/jacs.5c09579
CrossrefPubMedSuche in Google Scholar
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Keywords

(±)-harziandione - harziane diterpenoids - Giese-type addition - photocatalytic deoxygenative alkylation - intramolecular aldol condensation - Chugaev-type elimination - acyl radical cyclization

Significance

Gui and co-workers report the total synthesis of harziane diterpenoid (±)-harziandione. The natural product features a 6 /5 /7 /4 tetracyclic core including a bridged [3.2.1] ring system. Bioactivity studies have shown a variety of medicinally relevant properties, ranging from antifungal activity to cytotoxicity against human cancer cell lines, leading to an increased demand for synthetic access to these natural products.


Comment

Starting from cyclobutane A, diketone C is accessed via a Giese-type addition. Organolithium addition, photocatalytic deoxygenative alkylation and intramolecular aldol condensation forge tricyclic diol I. Chugaev-type elimination provides olefin K, which allows for synthesis of the [3.2.1] bicyclic motif in enone M via acyl radical cyclization.




Publikationsverlauf

Artikel online veröffentlicht:
30. Oktober 2025

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