ArticleChemical science2012
Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3 + 2] annulation.
Article in Chemical science, 2012. 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.
- Phosphine-Catalyzed (4+1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines through Phosphonium Diene Intermediates.ChemCatChem · 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
- Catalytic Asymmetric Total Synthesis of (-)-Actinophyllic Acid.Journal of the American Chemical Society · 2016Article
- Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.Aldrichimica acta · 2016Article
- Stereoselective Syntheses of α,β-Unsaturated γ-Amino Esters Through Phosphine-Catalyzed γ-Umpolung Additions of Sulfonamides to γ-Substituted Allenoates.Tetrahedron letters · 2015Article
- The ever-expanding role of asymmetric covalent organocatalysis in scalable, natural product synthesis.Natural product reports · 2014Review
- Hydroxyproline-derived pseudoenantiomeric [2.2.1] bicyclic phosphines: asymmetric synthesis of (+)- and (-)-pyrrolines.Journal of the American Chemical Society · 2014Article
- Phosphine catalysis of allenes with electrophiles.Chemical Society reviews · 2014Review
- Chiral phosphines in nucleophilic organocatalysis.Beilstein journal of organic chemistry · 2014Review
- Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.Chemical communications (Cambridge, England) · 2013Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
In this study we performed the total synthesis of the terpene indole alkaloid (+)-ibophyllidine through a pathway involving asymmetric phosphine catalysis, with our novel l-4-hydroxyproline-derived chiral phosphine mediating the key [3 + 2] annulation. Hydrogenation of the [3 + 2] adduct allowed the rapid formation of the stereochemically dense pyrrolidine ring of (+)-ibophyllidine in excellent yield with exceptionally high levels of both diastereo- and enantioselectivity. We constructed the remainder of the pentacyclic skeleton through an intramolecular alkylation and an intramolecular aza-Morita-Baylis-Hillman reaction.
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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 Socratic graph.