ArticleJournal of the American Chemical Society2025
Total Synthesis of (-)-Neocucurbol C Enabled by Pattern Recognition and MHAT Cyclization.
Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Total Synthesis of (±)-Stemocurtisine via Catalytic Carbonylation.Journal of the American Chemical Society · 2026Article
- Total syntheses of (+)-dalesconols A and B enabled by triple-relayed remote chirality transfer.Nature communications · 2026Article
- Seven-Step Total Synthesis of Conidiogenone B Enabled by Radical Cyclizations.Journal of the American Chemical Society · 2026Article
- Collective Total Synthesis of a Unique Class of Liverworts-Derived Cembrane Diterpenoids.Angewandte Chemie (International ed. in English) · 2025Article
- Total Synthesis of (-)-Psathyrin A Enabled by Radical Cyclization.Journal of the American Chemical Society · 2025Article
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Authors and funding
9 authors.
Funding
Abstract
We report an asymmetric total synthesis of (-)-neocucurbol C, a diterpene natural product possessing a unique and complex 6/6/5/5/6 polycyclic skeleton and nine stereocenters. Pattern-recognition analysis led us to the chiral pool molecule (+)-nootkatone as the starting material, already containing the AB ring system and two key stereocenters encoded by the target molecule. The extra isopropenyl group of (+)-nootkatone was removed by Kwon's hydrodealkenylative bond fragmentation. Other key steps include a Suzuki-Miyaura cross coupling to introduce an aromatic ring as the E ring precursor, an oxidative dearomatization cyclization to form the key oxa-bridge, and a metal-catalyzed hydrogen atom transfer (MHAT)-initiated reductive radical cyclization to complete the entire framework for subsequent peripheral decorations, which eventually delivered (-)-neocucurbol C in 24 steps for the first time. In addition, the cytotoxicity evaluation of (-)-neocucurbol C and its synthetic intermediates against multiple cancer cell lines identified new lead compounds with promising anticancer activity for further development.
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