ArticleJournal of the American Chemical Society2021
A General Iridium-Catalyzed Reductive Dienamine Synthesis Allows a Five-Step Synthesis of Catharanthine via the Elusive Dehydrosecodine.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Iridium-Catalyzed Reductive Deoxygenation of Esters for the Synthesis of Sterically Hindered Ethers.Angewandte Chemie (International ed. in English) · 2025Article
- Total Synthesis of Isodaphlongamine H by Iridium-Catalyzed Reductive [3 + 2] Cycloaddition of N-Hydroxylactam.Angewandte Chemie (International ed. in English) · 2025Article
- Regioselective Synthesis of β,γ-Unsaturated Amides from Unactivated Alkenes.The Journal of organic chemistry · 2025Article
- Merging SOMO activation with transition metal catalysis: Deoxygenative functionalization of amides to β-aryl amines.Science advances · 2025Article
- 1,2-Redox Transpositions of Tertiary Amides.Journal of the American Chemical Society · 2023Article
- Challenges and Breakthroughs in Selective Amide Activation.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Review
- Challenges and Breakthroughs in Selective Amide Activation.Angewandte Chemie (International ed. in English) · 2022Review
- Multicatalysis protocol enables direct and versatile enantioselective reductive transformations of secondary amides.Science advances · 2022Article
- Difluoroalkylation of Tertiary Amides and Lactams by an Iridium-Catalyzed Reductive Reformatsky Reaction.Organic letters · 2022Article
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Authors and funding
4 authors.
Funding
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Abstract
A new reductive strategy for the stereo- and regioselective synthesis of functionalized isoquinuclidines has been developed. Pivoting on the chemoselective iridium(I)-catalyzed reductive activation of β,γ-unsaturated δ-lactams, the efficiently produced reactive dienamine intermediates readily undergo [4 + 2] cycloaddition reactions with a wide range of dienophiles, resulting in the formation of bridged bicyclic amine products. This new synthetic approach was extended to aliphatic starting materials, resulting in the efficient formation of cyclohexenamine products, and readily applied as the key step in the shortest (five-step) total synthesis of vinca alkaloid catharanthine to date, proceeding via its elusive biosynthetic precursor, dehydrosecodine.
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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.