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Synthesis of Aminoalkyl Sclareolide Derivatives and Antifungal Activity Studies.

Ziyi LiHua GaoHaibo MeiGuangwei WuVadim A SoloshonokJianlin Han
Published in: Molecules (Basel, Switzerland) (2023)
Sclareolide was developed as an efficient C -nucleophilic reagent for an asymmetric Mannich addition reaction with a series of N - tert -butylsulfinyl aldimines. The Mannich reaction was carried out under mild conditions, affording the corresponding aminoalkyl sclareolide derivatives with up to 98% yield and 98:2:0:0 diastereoselectivity. Furthermore, the reaction could be performed on a gram scale without any reduction in yield and diastereoselectivity. Additionally, deprotection of the obtained Mannich addition products to give the target sclareolide derivatives bearing a free N-H group was demonstrated. In addition, target compounds 4 - 6 were subjected to an antifungal assay in vitro, which showed considerable antifungal activity against forest pathogenic fungi.
Keyphrases
  • structure activity relationship
  • climate change
  • high throughput
  • gram negative
  • candida albicans
  • electron transfer
  • solid state