Stereoselective Total Synthesis of the Putative Structure of Nitraraine

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 1H NMR data of tangutorine. The unambiguous synthesis of 5 is reported from tryp...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-08, Vol.79 (16), p.7740-7745
Main Authors: Arioli, Federica, Pérez, Maria, Subrizi, Fabiana, Llor, Núria, Bosch, Joan, Amat, Mercedes
Format: Article
Language:English
Subjects:
Alcaloides
Alkaloids
Alkaloids - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Carbolines - chemical synthesis
Carbolines - chemistry
Compostos heterocíclics
Esters
Heterocyclic compounds
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Lactames
Lactams
Lactams - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Organic synthesis
Quinolizines - chemical synthesis
Quinolizines - chemistry
Stereoisomerism
Síntesi orgànica
Triptòfan
Tryptophan
Tryptophan - analogs & derivatives
Tryptophan - chemistry
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Summary: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 1H 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 1H NMR data of 5 did not match those reported for the natural product.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5013543