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Partialsynthese der Nikkomycine B x und K x sowie unnatürlicher Stereoisomerer und Strukturanaloga
Author(s) -
Hahn Holger,
Heitsch Holger,
Rathmann Ralph,
Zimmermann Gesine,
Bormann Christiane,
Zähner Hans,
König Wilfried A.
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870832
Subject(s) - chemistry , stereochemistry , derivative (finance) , economics , financial economics
Partial Synthesis of Nikkomycins B x , K x and Unnatural Stereoisomers and Structural Analogues Nikkomycin B x ( 8a ) was prepared by connecting synthetic (2 S ,3 S ,4 S )‐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(3 H )‐one ( 6a ). In an analogous way the (2 S ,3 R ,4 R )‐stereoisomer 8b , the p ‐methoxy derivative 8c , nikkomycin K x ( 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.