Please use this identifier to cite or link to this item: http://hdl.handle.net/2445/99223
Title: Stereoselective total synthesis of the putative structure of nitraraine
Author: Arioli, Federica
Pérez Bosch, Maria
Subrizi, F.
Llor Brunés, Núria
Bosch Cartes, Joan
Amat Tusón, Mercedes
Keywords: Alcaloides
Síntesi orgànica
Lactames
Compostos heterocíclics
Triptòfan
Alkaloids
Organic synthesis
Lactams
Heterocyclic compounds
Tryptophan
Issue Date: 15-Aug-2014
Publisher: American Chemical Society
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.
Note: Versió postprint del document publicat a: http://dx.doi.org/10.1021/jo5013543
It is part of: Journal of Organic Chemistry, 2014, vol. 79, num. 16, p. 7740-7745
Related resource: http://dx.doi.org/10.1021/jo5013543
URI: http://hdl.handle.net/2445/99223
ISSN: 0022-3263
Appears in Collections:Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

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