Terminal Alkynes as One‐Carbon Donors in (5+1) Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B
Abstract: Transition‐metal‐catalyzed [4+2] heteroannulation of α,β‐unsaturated oximes and their derivatives with alkynes has been developed into a powerful strategy for the synthesis of pyridines. It nevertheless lacks regioselectivity when unsymmetrically substituted alkynes are used. We report herein the unprecedented synthesis of polysubstituted pyridines by a formal [5+1] heteroannulation of two readily accessible building blocks. A copper‐catalyzed aza‐Sonogashira cross‐coupling between β,γ‐unsaturated oxime esters and terminal alkynes affords ynimines, which, without isolation, undergo an acid‐catalyzed domino reaction involving ketenimine formation, 6π‐electrocyclization and aromatization to afford pyridines. Terminal alkynes served as a one‐carbon donor to the pyridine core in this transformation. Di‐ through pentasubstituted pyridines are accessible with complete regioselectivity and excellent functional‐group compatibility. The first total synthesis of anibamine B, an indolizinium alkaloid with potent antiplasmodial activity, was accomplished featuring this reaction as a key step.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Terminal Alkynes as One‐Carbon Donors in (5+1) Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B ; day:21 ; month:04 ; year:2023 ; extent:7
Angewandte Chemie ; (21.04.2023) (gesamt 7)
- Creator
- DOI
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10.1002/ange.202303537
- URN
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urn:nbn:de:101:1-2023042415474202090996
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:58 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Lavernhe, Rémi
- Wang, Qian
- Zhu, Jieping
Other Objects (12)
Terminal Alkynes as One‐Carbon Donors in (5+1) Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B
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ENAMINONES AS BULDING BLOCKS IN ORGANIC SYNTHESIS: SYNTHESIS OF NEW POLYFUNCTIONAL PYRIDINES, CONDENSED PYRIDINES AND ΡΕΝΤΑ SUBSTITUTED BENZENE
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Terminal Alkynes as One‐Carbon Donors in (5+1) Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B
Mn(III)-Mediated Synthesis of Pyridines
Lecture 13: Reactions, Synthesis, & Alkynes
Regiodivergent Arylation of Pyridines via Zincke Intermediates
Regiodivergent Arylation of Pyridines via Zincke Intermediates
Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines
Tandem One-Pot Synthesis of Polysubstituted Pyridines
ENAMINONES AS BULDING BLOCKS IN ORGANIC SYNTHESIS: SYNTHESIS OF NEW POLYFUNCTIONAL PYRIDINES, CONDENSED PYRIDINES AND ΡΕΝΤΑ SUBSTITUTED BENZENE
Alkynes: de-novo synthesis and substrate functionalization
Direct Catalytic Synthesis of Ynamides from Alkynes
Nitrene Radical Intermediates in Catalytic Synthesis
A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines
Terminal Alkynes as One‐Carbon Donors in (5+1) Heteroannulation: Synthesis of Pyridines via Ynimine Intermediates and Application in the Total Synthesis of Anibamine B
Mn(III)-Mediated Synthesis of Pyridines
Lecture 13: Reactions, Synthesis, & Alkynes
Regiodivergent Arylation of Pyridines via Zincke Intermediates
Regiodivergent Arylation of Pyridines via Zincke Intermediates
Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines
Tandem One-Pot Synthesis of Polysubstituted Pyridines
ENAMINONES AS BULDING BLOCKS IN ORGANIC SYNTHESIS: SYNTHESIS OF NEW POLYFUNCTIONAL PYRIDINES, CONDENSED PYRIDINES AND ΡΕΝΤΑ SUBSTITUTED BENZENE
Alkynes: de-novo synthesis and substrate functionalization
Direct Catalytic Synthesis of Ynamides from Alkynes
Nitrene Radical Intermediates in Catalytic Synthesis