ArticleJournal of the American Chemical Society2018
A Benzyne Insertion Approach to Hetisine-Type Diterpenoid Alkaloids: Synthesis of Cossonidine (Davisine).
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Total Synthesis of Aconicarmisulfonine A, a Sulfonated Diterpene Alkaloid.Journal of the American Chemical Society · 2025Article
- The Versatile and StrategicChemical reviews · 2024Review
- Evaluation of Retro-Aldol vs Retro-Carbonyl-Ene Mechanistic Pathways in a Complexity-Generating C-C Bond Fragmentation.Organic letters · 2024Article
- Switchable chemoselective aryne reactions between nucleophiles and pericyclic reaction partners using either 3-methoxybenzyne or 3-silylbenzyne.Nature communications · 2024Article
- Finding activity through rigidity: syntheses of natural products containing tricyclic bridgehead carbon centers.Natural product reports · 2023Review
- Dearomative logic in natural product total synthesis.Natural product reports · 2022Review
- Review
- A donor-acceptor complex enables the synthesis ofChemical science · 2021Article
- Structure, property, biogenesis, and activity of diterpenoid alkaloids containing a sulfonic acid group fromActa pharmaceutica Sinica. B · 2020Article
- A Case for Bond-Network Analysis in the Synthesis of Bridged Polycyclic Complex Molecules: Hetidine and Hetisine Diterpenoid Alkaloids.Angewandte Chemie (International ed. in English) · 2020Review
- Silyl Tosylate Precursors to Cyclohexyne, 1,2-Cyclohexadiene, and 1,2-Cycloheptadiene.Organic letters · 2020Article
- Safety Assessment of Benzyne Generation from a Silyl Triflate Precursor.Organic letters · 2020Article
- Cycloadditions of Oxacyclic Allenes and a Catalytic Asymmetric Entryway to Enantioenriched Cyclic Allenes.Angewandte Chemie (International ed. in English) · 2019Article
- Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors.The Journal of organic chemistry · 2019Article
Corrections and comments
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Authors and funding
9 authors.
Funding
Abstract
The hetisine-type natural products exhibit one of the most complex carbon skeletons within the diterpenoid alkaloid family. The use of network analysis has enabled a synthesis strategy to access alkaloids in this class with hydroxylation on the A-ring. Key transformations include a benzyne acyl-alkylation to construct a key fused 6-7-6 tricycle, a chemoselective nitrile reduction, and sequential C-N bond formations using a reductive cyclization and a photochemical hydroamination to construct an embedded azabicycle. Our strategy should enable access to myriad natural and unnatural products within the hetisine-type.
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Registered trials
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