ArticleScience (New York, N.Y.)2023
Total synthesis of lissodendoric acid A via stereospecific trapping of a strained cyclic allene.
Article in Science (New York, N.Y.), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Complete Computational Exploration of Eight-Carbon Hydrocarbon Chemical Space.The Journal of organic chemistry · 2026Article
- Enantioselective Synthesis ofJACS Au · 2026Article
- Photochemistry of an Anti-Bredt Olefin through the Lens of Multistate Multireference Quantum Chemistry.Journal of the American Chemical Society · 2026Article
- Seven-Membered Azacyclic Allenes: Synthesis, Trapping, and Stereochemical Transfer Studies.Journal of the American Chemical Society · 2026Article
- The Diels-Alder Reaction as a Key Step in Natural Product Synthesis.Progress in the chemistry of organic natural products · 2026Review
- Development of a Vinylated Cyclic Allene: A Fleeting Strained Diene for the Diels-Alder Reaction.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis and reactivity of nitrogen-containing strained cyclic 1,2,3-trienes.Nature synthesis · 2025Article
- Geometric distortion as an enabling tool for organic synthesis.Nature synthesis · 2025Article
- Article
- Recent advancements in the chemistry of Diels-Alder reaction for total synthesis of natural products: a comprehensive review (2020-2023).RSC advances · 2025Review
- A solution to the anti-Bredt olefin synthesis problem.Science (New York, N.Y.) · 2024Article
- Total Synthesis of Lissodendoric Acid A.Angewandte Chemie (International ed. in English) · 2024Article
- Diels-Alder Cycloadditions of Oxacyclic Allenes and α-Pyrones.Organic letters · 2024Article
- Access to Complex Scaffolds Through [2 + 2] Cycloadditions of Strained Cyclic Allenes.Journal of the American Chemical Society · 2024Article
- Evaluation of Retro-Aldol vs Retro-Carbonyl-Ene Mechanistic Pathways in a Complexity-Generating C-C Bond Fragmentation.Organic letters · 2024Article
- Generation and reactivity of unsymmetrical strained heterocyclic allenes.Nature synthesis · 2024Article
- Cyclic Allene Approach to the Manzamine Alkaloid Keramaphidin B.Organic letters · 2023Article
- Article
- Catalyst-Controlled Annulations of Strained Cyclic Allenes with π-Allylpalladium Complexes.Journal of the American Chemical Society · 2023Article
- Total synthesis of lissodendoric acid A via stereospecific trapping of a strained cyclic allene.Science (New York, N.Y.) · 2023Article
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Authors and funding
7 authors.
Funding
Abstract
Small rings that contain allenes are unconventional transient compounds that have been known since the 1960s. Despite being discovered around the same time as benzyne and offering a number of synthetically advantageous features, strained cyclic allenes have seen relatively little use in chemical synthesis. We report a concise total synthesis of the manzamine alkaloid lissodendoric acid A, which hinges on the development of a regioselective, diastereoselective, and stereospecific trapping of a fleeting cyclic allene intermediate. This key step swiftly assembles the azadecalin framework of the natural product, allows for a succinct synthetic endgame, and enables a 12-step total synthesis (longest linear sequence; 0.8% overall yield). These studies demonstrate that strained cyclic allenes are versatile building blocks in chemical synthesis.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.