ArticleJournal of the American Chemical Society2016
Catalytic Asymmetric Total Synthesis of (-)-Actinophyllic Acid.
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 16 papers.
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Who cites it
16 citing papers in PubMed.
- Diastereoselective Radical 1,4-Ester Migration: Radical Cyclizations of Acyclic Esters with SmIJournal of the American Chemical Society · 2022Article
- Chiral Allenylcarbonyls - Underexploited Building Blocks for Complex Synthesis.Letters in organic chemistry · 2022Article
- Samarium(ii) iodide-mediated reactions applied to natural product total synthesis.RSC advances · 2022Review
- Recent advances in the chemistry of ketyl radicals.Chemical Society reviews · 2021Article
- SmIJournal of the American Chemical Society · 2021Article
- Phosphine-Catalyzed (4+1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines through Phosphonium Diene Intermediates.ChemCatChem · 2020Article
- Catalytic Enantiodivergent Michael Addition by Subtle Adjustment of Achiral Amino Moiety of Dipeptide Phosphines.iScience · 2020Article
- Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles.iScience · 2020Article
- Design, synthesis and application of a new type of bifunctionalChemical science · 2019Article
- Phosphine-Catalyzed α-Umpolung-Aldol Reaction for the Synthesis of Benzo[ b]azapin-3-ones.Organic letters · 2019Article
- Phosphine-Promoted [4 + 3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3 + 3] and [4 + 3] Pathways.RSC advances · 2019Article
- Discussion Addendum for: Phosphine-Catalyzed [3 + 2] Annulation: Synthesis of Ethyl 5-(Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2019Article
- Phosphine Organocatalysis.Chemical reviews · 2018Review
- Catalytic Enantioselective Synthesis of Guvacine Derivatives through [4 + 2] Annulations of Imines with α-Methylallenoates.Organic letters · 2018Article
- Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene-Imine [3 + 2] Annulation.ACS catalysis · 2018Article
- Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition-Wittig olefination.Chemical science · 2018Article
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3 authors.
Funding
Abstract
Described herein is a catalytic asymmetric total synthesis of (-)-actinophyllic acid, with the key step being a chiral phosphine-catalyzed [3 + 2] annulation between an imine and an allenoate to form a pyrroline intermediate in 99% yield and 94% ee. The synthesis also features CuI-catalyzed coupling between a ketoester and a 2-iodoindole to shape the tetrahydroazocine ring; intramolecular alkylative lactonization; SmI2-mediated intramolecular pinacol coupling between ketone and lactone subunits to assemble the complex skeleton of (-)-actinophyllic acid; and an unprecedented regioselective dehydroxylation.
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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 Socratic graph.