ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Partial Synthesis of Nikkomycins Bx, Kx and Unnatural Stereoisomers and Structural AnaloguesNikkomycin Bx (8a) was prepared by connecting synthetic (2S,3S,4S)-2-amino-4-hydroxy-4-(4-hydroxyphenyl)-3-methyl-butanoic acid (1a) to natural 1-(5′-amino-5-deoxy-β-D-allofuranuronosyl)-4-formyl-1H-imidazol-2(3H)-one (6a). In an analogous way the (2S,3R,4R)-stereoisomer 8b, the p-methoxy derivative 8c, nikkomycin Kx (8d), and its analogues 8e and 8f, as well as the nikkomycin Z analogues 8g and 8h were prepared. Of the synthetic products only the stereoisomers 8a and 8d, corresponding to the natural products, showed the expected fungicidal activity. The p-methoxyphenyl derivative 8c is only active against yeasts, while the nikkomycin analogues 8e-8h are inactive against fungi.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198719870832
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