Synthesis and Biological Evaluation of Highly Potent Fungicidal Deoxy‐Hygrophorones

Abstract

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.

Total synthesis and antimicrobial evaluation of (+)-hygrophorone B12 and its analogues

“…Therefore, we hypothesize that other hygrophorones such as B type show high antibacterial activity. According to our survey of the literature, antimicrobial susceptibility tests of other hygrophorones toward bacterial-pathogen-caused human infectious diseases have not yet been reported, albeit in 2021 Westermann’s group disclosed the fungicidal activity of hygrophorone B 12 ( 4 ) and its 6-deoxy analogue against plant pathogens 16 . Consequently, the development of efficient and flexible methods for the synthesis of the hygrophorone family, and the elucidation of their structure–activity relationship are desirable and useful from the viewpoint of medicinal/pharmaceutical chemistry.…”