ReviewACS central science2021
Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step.
Review in ACS central science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Article
- Skeletal Reorganization of Cycloalkylamines Into Angular Azatetracyclic Scaffolds.Angewandte Chemie (International ed. in English) · 2026Article
- Nitrosoarenes as Versatile Precursors forACS omega · 2026Article
- TiClOrganic letters · 2026Article
- An Unorthodox Enolate-Triggered Radical Relay Directs the Chemo Upgrading of Levulinic Acid Into Citramalic Acid.ChemSusChem · 2026Article
- Ring contraction and ring expansion reactions in terpenoid biosynthesis and their application to total synthesis.Beilstein journal of organic chemistry · 2026Review
- Divergent synthesis of Haplomitrium diterpenoids via a late-stage biomimetic skeletal reorganization approach.Nature communications · 2025Article
- Quinol-Enedione Rearrangement.Organic letters · 2025Article
- Chiral sulfide and achiral sulfonic acid cocatalyzed enantioselective electrophilic tandem selenylation semipinacol rearrangement of allenols.Nature communications · 2025Article
- Domino Reactions Enable Zn-Mediated Direct Synthesis of Spiro-Fused 2-Oxindole-α-Methylene-γ-Butyrolactones/Lactams from Isatin Derivatives and 2-(Bromomethyl)acrylates.Molecules (Basel, Switzerland) · 2024Article
- Recent Advances in the Domino Annulation Reaction of Quinone Imines.Molecules (Basel, Switzerland) · 2024Review
- Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-International journal of molecular sciences · 2024Article
- Deconstructive and Divergent Synthesis of Bioactive Natural Products.Molecules (Basel, Switzerland) · 2023Review
- Enantioselective total syntheses of six natural and two proposed meroterpenoids fromChemical science · 2023Article
- Expedient synthesis of spiro[3.3]heptan-1-ones via strain-relocating semipinacol rearrangements.Tetrahedron · 2023Article
- Unifying the Synthesis of a Whole Family of Marine Meroterpenoids through a Biosynthetically Inspired Sequence of 1,2-Hydride and Methyl Shifts as Key Step.Marine drugs · 2023Article
- Sigmatropic [1,5] Carbon Shift of Transient C3 Ammonium Enolates.Angewandte Chemie (International ed. in English) · 2022Article
- Recent development and applications of semipinacol rearrangement reactions.Chemical science · 2021Review
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The art of natural product total synthesis is closely associated with two major determinants: the development/application of novel chemical reactions and the innovation in strategic use of classic organic reactions. While purposely seeking/applying a new synthetic methodology allowing nonconventional bond disconnections could shorten the synthetic route, the development of domino processes composed of a series of well-established reactions could also lead to a concise, practical, and aesthetically appealing synthesis. As an important class of textbook reactions, the 1,2-anionotropic rearrangements discovered at the dawn of modern organic chemistry have important bearings not only on chemical synthesis but also on the conceptual breakthroughs in the field. In its basic form, the 1,2-shift affords nothing but a constitutional isomer of the starting material and is therefore not a complexity-generating transformation. However, such a simple 1,2-shift could in fact change the molecular topology if the precursor is cleverly designed. More dramatically, it can metamorphosize the structure of the substrate when it is combined with other transformations in a domino sequence. In this Outlook, we highlight recent examples of natural product synthesis featuring a key domino process incorporating a 1,2-anionotropic rearrangement. Specifically, domino reactions integrating Wagner-Meerwein, pinacol, α-ketol, α-aminoketone, α-iminol, or benzilic acid rearrangements will be discussed.
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Registered trials
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