ArticleOrganic letters2025
Decoding Guaianolide Biosynthesis: Synthetic Insights into Pseudoguaianolides and Seco-Guaianolides.
Article in Organic letters, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Oxidation-Induced Scaffold Remodeling inOrganic letters · 2026Article
- Further elaboration of the stereodivergent approach to chaetominine-type alkaloids: synthesis of the reported structures of aspera chaetominines A and B and revised structure of aspera chaetominine B.Beilstein journal of organic chemistry · 2025Article
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Abstract
The biosynthetic pathways leading to pseudoguaianolides and seco-guaianolides remain unclear. In this work, we demonstrate that highly oxidized 8,12-guaianolides serve as unprecedented precursors, enabling chemoselective, one-step access to pseudoguaianolide, seco-guaianolide, and xanthanolide-type sesquiterpenoids. Key mechanistic insights reveal the pivotal role of peroxide substituents on the guaianolide core and stereoelectronic factors in controlling reaction outcomes. These findings shed light on guaianolide selectivity and may mirror actual biosynthetic pathways, offering transformative potential for oxidative transformations in sesquiterpenoid synthesis.
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