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2014-08-15

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/99223

Stereoselective total synthesis of the putative structure of nitraraine

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Abstract

After the structure originally proposed for nitraraine was shown to be incorrect by total synthesis, the alternative structure 5 was recently suggested for the alkaloid on biosynthetic grounds and by comparison with the (1)H NMR data of tangutorine. The unambiguous synthesis of 5 is reported from tryptophanol and ketodiester 6, via oxazoloquinolone lactam 7. However, the melting point and (1)H NMR data of 5 did not match those reported for the natural product.

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http://dx.doi.org/10.1021/jo5013543

Subject

Alcaloides, Síntesi orgànica, Lactames, Compostos heterocíclics, Triptòfan

Subject (English)

Alkaloids, Organic synthesis, Lactams, Heterocyclic compounds, Tryptophan

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

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ARIOLI, Federica, et al. Stereoselective total synthesis of the putative structure of nitraraine. Journal of Organic Chemistry. 2014. Vol. 79, num. 16, pags. 7740-7745. ISSN 0022-3263. [consulted: 7 of October of 2026]. Available at: https://hdl.handle.net/2445/99223

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