ArticleThe Journal of organic chemistry2018
Development of a Unified Enantioselective, Convergent Synthetic Approach Toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Asymmetric Formation of the Polycyclic Norditerpenoid Carbocyclic Core by Tandem Annulation Cascade.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Asymmetric Total Synthesis of (+)-Ineleganolide.Angewandte Chemie (International ed. in English) · 2026Article
- Short, Enantioselective Total Synthesis of (+)-Ineleganolide.Journal of the American Chemical Society · 2025Article
- Morphology of lithium halides in tetrahydrofuran from molecular dynamics with machine learning potentials.Chemical science · 2024Article
- Total Synthesis of the Norcembranoid Scabrolide B and Its Transformation into Sinuscalide C, Ineleganolide, and Horiolide.Journal of the American Chemical Society · 2024Article
- A Comprehensive Review of the Classification, Sources, Phytochemistry, and Pharmacology of Norditerpenes.Molecules (Basel, Switzerland) · 2023Review
- A Convergent Total Synthesis of (+)-Ineleganolide.Journal of the American Chemical Society · 2023Article
- Total Syntheses of (+)-Ineleganolide and (-)-Sinulochmodin C.Journal of the American Chemical Society · 2022Article
- Total Syntheses of Scabrolide A and Nominal Scabrolide B.Journal of the American Chemical Society · 2022Article
- Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications.Chemical reviews · 2021Article
- Diazocarbonyl and Related Compounds in the Synthesis of Azoles.Molecules (Basel, Switzerland) · 2021Review
- The Allylic Alkylation of Ketone Enolates.ChemistryOpen · 2020Review
- Pharmacophore-Directed Retrosynthesis Applied to Rameswaralide: Synthesis and Bioactivity ofOrganic letters · 2019Article
- Correction: Enantioselective, convergent synthesis of the ineleganolide core by a tandem annulation cascade.Chemical science · 2019Article
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Authors and funding
6 authors.
Funding
Abstract
An enantioselective and diastereoselective approach toward the synthesis of the tetracyclic scaffold of the furanobutenolide-derived polycyclic norditerpenoids is described. Focusing on synthetic efforts toward ineleganolide, the synthetic approach utilizes a palladium-catalyzed enantioselective allylic alkylation for the construction of the requisite chiral tertiary ether. A diastereoselective cyclopropanation-Cope rearrangement cascade enabled the convergent assembly of the ineleganolide [6,7,5,5]-tetracyclic scaffold. Investigation of substrates for this critical tandem annulation process is discussed along with synthetic manipulations of the [6,7,5,5]-tetracyclic scaffold and the attempted interconversion of the [6,7,5,5]-tetracyclic scaffold of ineleganolide to the isomeric [7,6,5,5]-core of scabrolide A and its naturally occurring isomers. Computational evaluation of ground-state energies of late-stage synthetic intermediates was used to guide synthetic development and aid in the investigation of the conformational rigidity of these highly constrained and compact polycyclic structures.
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