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2018

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cc-by (c) Plesniak, Mateusz P. et al., 2018
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/178759

Samarium(II) folding cascades involving hydrogen atom transfer for the synthesis of complex polycycles

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https://doi.org/10.1038/s41467-018-07194-x

Abstract

The expedient assembly of complex, natural product-like small molecules can deliver new chemical entities with the potential to interact with biological systems and inspire the development of new drugs and probes for biology. Diversity-oriented synthesis is a particularly attractive strategy for the delivery of complex molecules in which the 3-dimensional architecture varies across the collection. Here we describe a folding cascade approach to complex polycyclic systems bearing multiple stereocentres mediated by reductive single electron transfer (SET) from SmI2. Simple, linear substrates undergo three different folding pathways triggered by reductive SET. Two of the radical cascade pathways involve the activation and functionalization of otherwise inert secondary alkyl and benzylic groups by 1,5-hydrogen atom transfer (HAT). Combination of SmI2, a privileged reagent for cascade reactions, and 1,5-HAT can lead to complexity-generating radical sequences that unlock access to diverse structures not readily accessible by other means.

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Síntesi orgànica, Productes naturals, Compostos heterocíclics, Química heterocíclica

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Organic synthesis, Natural products, Heterocyclic compounds, Heterocyclic chemistry

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

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PLESNIAK, Mateusz P., et al. Samarium(II) folding cascades involving hydrogen atom transfer for the synthesis of complex polycycles. Nature Communications. 2018. Vol. 9, num. 4802. ISSN 2041-1723. [consulted: 17 of August of 2026]. Available at: https://hdl.handle.net/2445/178759

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