A new approach towards ikimine A analogues

Natural Product Research
Jürgen KraussFranz Bracher

Abstract

An analogon of the alkylpyridine alkaloid ikimine A (1) was prepared in six steps starting from undec-10-ynoic acid. A key step in this synthesis was a Sonogashira coupling of the alkyne and 3-iodopyridine, followed by hydrogenation of the alkyne, reduction of the ester to the primary alcohol and oxidation to the corresponding aldehyde. This aldehyde was converted to the ikimine A analogon with O-methyl hydroxylamine hydrochloride. This product and the intermediate alkylpyridines were tested in the agar diffusion assay for antibacterial and antifungal activities.

References

Oct 25, 2001·The Journal of Organic Chemistry·George A. Kraus, Alex Melekhov
Apr 12, 2003·The Journal of Organic Chemistry·Yao WangRichard C Larock

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Citations

Mar 28, 2017·Chemistry : a European Journal·Luca CapaldoDavide Ravelli
Mar 6, 2007·Archiv der Pharmazie·Jürgen KraussFranz Bracher

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Methods Mentioned

BETA
NMR

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