ArticleJournal of the American Chemical Society2022
Catalysis-Enabled 13-Step Total Synthesis of (-)-Peyssonnoside A.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- 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
- Total Synthesis of (-)-Psathyrin A Enabled by Radical Cyclization.Journal of the American Chemical Society · 2025Article
- Biosynthesis of the Red Algal Diterpene Peyssonnosol in Bacteria.Angewandte Chemie (International ed. in English) · 2025Article
- Total Synthesis of (-)-Neocucurbol C Enabled by Pattern Recognition and MHAT Cyclization.Journal of the American Chemical Society · 2025Article
- Studies toward the synthesis of yaretol: an unexpected rearrangement en route to the tricyclic core.Tetrahedron · 2025Article
- Exploring and expanding the natural chemical space of bacterial diterpenes.Nature communications · 2025Article
- Total Syntheses of Phleghenrines A and C.Organic letters · 2023Article
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Authors and funding
3 authors.
Funding
Abstract
We report a 13-step enantioselective and stereoselective total synthesis of (-)-peyssonnoside A, a unique diterpene glucoside with a rare and highly congested pentasubstituted cyclopropane and promising antimicrobial activity. Among the 10 steps to synthesize (-)-peyssonnosol, the aglycone of (-)-peyssonnoside A, eight transition-metal-catalyzed transformations enabled the construction of all new C-C bonds and stereocenters without involving any protecting groups. Notably, a palladium-catalyzed dearomative cyclization was used to build the C-6 spiro all-carbon quaternary center, and a counterintuitive hydrogen atom transfer (HAT)-initiated reductive olefin cross-coupling was realized to forge the pentasubstituted cyclopropane ring with excellent stereoselectivity.
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