ArticleJournal of the American Chemical Society2016
Catalytic Carbonylative Spirolactonization of Hydroxycyclopropanols.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
What it found
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The trial behind it
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Who cites it
25 citing papers in PubMed.
- Total Synthesis of (±)-Stemocurtisine via Catalytic Carbonylation.Journal of the American Chemical Society · 2026Article
- Ten-Step Total Synthesis of (±)-Phaeocaulisin A Enabled by Cyclopropanol Ring-Opening Carbonylation.Journal of the American Chemical Society · 2024Article
- Catalytic asymmetric intramolecular propargylation of cyclopropanols to access the cuparane core.Chemical science · 2024Article
- Convergent and Efficient Total Synthesis of (+)-Heilonine Enabled by C-H Functionalizations.Journal of the American Chemical Society · 2024Article
- Palladium-Catalyzed Carbonylative Difunctionalization of Unactivated Alkenes Initiated by Unstabilized Enolates.Angewandte Chemie (International ed. in English) · 2023Article
- A Bischler-Napieralski and homo-Mannich sequence enables diversified syntheses of sarpagine alkaloids and analogues.Nature communications · 2023Article
- Palladium-Catalyzed Carbonylations: Application in Complex Natural Product Total Synthesis and Recent Developments.The Journal of organic chemistry · 2023Review
- Synthesis of BenzofusedOrganometallics · 2022Article
- Redox-neutral manganese-catalyzed synthesis of 1-pyrrolines.Chemical science · 2022Article
- Catalysis-Enabled Concise and Stereoselective Total Synthesis of the Tricyclic Prostaglandin DAngewandte Chemie (International ed. in English) · 2022Article
- Immunosuppressive Sesquiterpenoids from the Edible MushroomJournal of fungi (Basel, Switzerland) · 2021Article
- Flow Chemistry-Enabled Divergent and Enantioselective Total Syntheses of Massarinolin A, Purpurolides B, D, E, 2,3-Deoxypurpurolide C, and Structural Revision of Massarinolin A.Angewandte Chemie (International ed. in English) · 2021Article
- A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones.International journal of molecular sciences · 2021Review
- Cu-catalyzed hydroxycyclopropanol ring-opening cyclization to tetrahydrofurans and tetrahydropyrans: short total syntheses of hyperiones.Chemical science · 2020Article
- Catalytic Hydroxycyclopropanol Ring-Opening Carbonylative Lactonization to Fused Bicyclic Lactones.Journal of the American Chemical Society · 2020Article
- Mechanistic Study of Isotactic Poly(propylene oxide) Synthesis using a Tethered Bimetallic Chromium Salen Catalyst.ACS catalysis · 2020Article
- Pyrrole Strategy for the γ-Lactam-ContainingOrganic letters · 2020Article
- Total Synthesis of trans-Resorcylide via Macrocyclic Stille Carbonylation.The Journal of antibiotics · 2019Article
- Total Synthesis, Biological Evaluation, and Target Identification of Rare Abies Sesquiterpenoids.Journal of the American Chemical Society · 2018Article
- Total Syntheses of Bisdehydroneostemoninine and Bisdehydrostemoninine by Catalytic Carbonylative Spirolactonization.Angewandte Chemie (International ed. in English) · 2018Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
A palladium-catalyzed cascade carbonylative spirolactonization of hydroxycyclopropanols has been developed to efficiently synthesize oxaspirolactones common to many complex natural products of important therapeutic value. The mild reaction conditions, high atom economy, broad substrate scope, and scalability of this new method were highlighted in expedient total syntheses of the Turkish tobacco natural products α-levantanolide and α-levantenolide in two and four steps, respectively. The hydroxycyclopropanol substrates are readily available in one step via a Kulinkovich reaction of the corresponding lactones. Mechanistic studies utilizing high-resolution electrospray ionization mass spectrometry (ESI-MS) identified several key intermediates in the catalytic cycle, as well as those related to catalyst decomposition and competitive pathways.
Identifiers
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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.