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Synthesis and Biological Evaluation of Highly Potent Fungicidal Deoxy ‐Hygrophorones
Author(s) -
Ditfe Toni,
Bette Eileen,
N. Sultani Haider,
Otto Alexander,
Wessjohann Ludger A.,
Arnold Norbert,
Westermann Bernhard
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100729
Subject(s) - chemistry , fungicide , aldehyde , stereochemistry , side chain , ring (chemistry) , organic chemistry , botany , catalysis , polymer , biology
Based on naturally occurring hygrophorones, racemic di‐ and mono‐hydroxylated cyclopentenones bearing an aliphatic side chain have been produced in short synthetic sequences starting from furfuryl aldehyde. For the series of dihydroxylated trans ‐configured derivatives, an Achmatowicz‐rearrangement and a Caddick‐ring contraction were employed, and for the series of trans ‐configured mono‐hydroxylated derivatives a Piancatelli‐rearrangement. All final products showed good to excellent fungicidal activities against the plant pathogens B. cinerea , S. tritici and P. infestans .