ArticleJournal of the American Chemical Society2019
A Chlorine-Atom-Controlled Terminal-Epoxide-Initiated Bicyclization Cascade Enables a Synthesis of the Potent Cytotoxins Haterumaimides J and K.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- A Chlorine-Bearing Asymmetric Center as a Stereocontrol Element in a Short Formal Synthesis of Steviol.Synthesis · 2025Article
- Unexpected Regiochemical Control in the Nugent-RajanBabu Reductive Epoxide Cyclization.Synthesis · 2025Article
- Synthesis of Differentially Halogenated Lissoclimide Analogues To Probe Ribosome E-Site Binding.ACS chemical biology · 2025Article
- Biomimetic chlorine-induced polyene cyclizations harnessing hypervalent chloroiodane-HFIP assemblies.Chemical science · 2023Article
- The Recurring Roles of Chlorine in Synthetic and Biological Studies of the Lissoclimides.Accounts of chemical research · 2021Review
- Stereocontrolled Radical Bicyclizations of Oxygenated Precursors Enable Short Syntheses of Oxidized Abietane Diterpenoids.Journal of the American Chemical Society · 2021Article
- Cobalt-Catalyzed Hydrogen-Atom Transfer Induces Bicyclizations that Tolerate Electron-Rich and Electron-Deficient Intermediate Alkenes.Angewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
Haterumaimide J (hatJ) is reportedly the most cytotoxic member of the lissoclimide family of labdane diterpenoids. The unusual functional group arrangement of hatJ-C18 oxygenation and C2 chlorination-resisted our efforts at synthesis until we adopted an approach based on rarely studied terminal epoxide-based cation-π bicyclizations that is described herein. Using the C2-chlorine atom as a key stereocontrol element and a furan as a nucleophilic terminator, the key structural features of hatJ were rapidly constructed. The 18-step stereoselective synthesis features applications of chiral pool starting materials, and catalyst-, substrate-, and auxiliary-based stereocontrol. Access to hatJ and its acetylated congener hatK permitted their biological evaluation against aggressive human cancer cell lines.
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