Synthesis of dienes from pyrrolidines using skeletal modification
Saturated N-heterocyclic pyrrolidines are common in natural products, medicinal compounds and agrochemicals. However, reconstruction of their skeletal structures creating new chemical space is a challenging task, and limited methods exist for this purpose. In this study, we report a skeletal modific...
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Veröffentlicht in: | Nature communications 2023-11, Vol.14 (1), p.7307-7307, Article 7307 |
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Sprache: | eng |
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Zusammenfassung: | Saturated N-heterocyclic pyrrolidines are common in natural products, medicinal compounds and agrochemicals. However, reconstruction of their skeletal structures creating new chemical space is a challenging task, and limited methods exist for this purpose. In this study, we report a skeletal modification strategy for conversion of polar cyclic pyrrolidines into nonpolar linear dienes through a N-atom removal and deconstruction process. This involves N-sulfonylazidonation followed by rearrangement of the resulting sulfamoyl azide intermediates. This can be an energetically unfavorable process, which involves the formation of active C–C π bonds, the consumption of inert C–N and C–C σ bonds and the destruction of stable five-membered rings, but we have used it here to produce versatile conjugated and nonconjugated dienes with links of varying lengths. We also studied the application of this method in late-stage skeletal modification of bioactive compounds, formal traceless C(sp
2
)–H functionalization and formal N-atom deletion.
Saturated N-heterocyclic pyrrolidines are common in natural products and medicinal compounds, but reconstruction of their skeletal structures to access new chemical space is a challenging. Here, the authors report a skeletal modification strategy for conversion of polar cyclic pyrrolidines into nonpolar linear dienes through a N-atom removal and deconstruction process. |
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ISSN: | 2041-1723 2041-1723 |
DOI: | 10.1038/s41467-023-43238-7 |