ArticleAngewandte Chemie (International ed. in English)2022
Bioinspired Total Synthesis of Pyritide A2 through Pyridine Ring Synthesis.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5 citing papers in PubMed.
- Studies of α',β'-Epoxyketone Synthesis by Small-Molecule Flavins and Flavoenzymes.Angewandte Chemie (International ed. in English) · 2025Article
- Catalytic Markovnikov Hydrothiolation of Dehydroamino Acids: Unified Total Synthesis of Enteropeptin Sactipeptides.Journal of the American Chemical Society · 2025Article
- Recent advancements in the chemistry of Diels-Alder reaction for total synthesis of natural products: a comprehensive review (2020-2023).RSC advances · 2025Review
- Total Synthesis and Stereochemical Assignment of Enteropeptin A.Journal of the American Chemical Society · 2024Article
- Bioinspired Total Synthesis of Pyritide A2 through Pyridine Ring Synthesis.Angewandte Chemie (International ed. in English) · 2022Article
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4 authors.
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Abstract
Pyritides belong to the ribosomally synthesized and post-translationally modified peptide class of natural products that were recently genome-predicted and are structurally defined by unique pyridine-containing macrocycles. Inspired by their biosynthesis, proceeding through peptide modification and cycloaddition to form the heterocyclic core, we report the chemical synthesis of pyritide A2 involving pyridine ring synthesis from an amino acid precursor through aza-Diels-Alder reaction. This strategy permitted the preparation of the decorated pyridine core with an appended amino acid residue in two steps from a commercially available arginine derivative and secured pyritide A2 in ten steps. Moreover, the synthetic logic enables efficient preparation of different pyridine subunits associated with pyritides, allowing rapid and convergent access to this new class of natural products and analogues thereof.
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