np7b00484_si_001.pdf (1.84 MB)
Gram-Scale, Stereoselective Synthesis and Biological Evaluation of (+)-Armillariol C
journal contribution
posted on 2017-08-21, 17:39 authored by M. Damoder Reddy, Hajime Kobori, Takumi Mori, Jing Wu, Hirokazu Kawagishi, E. Blake WatkinsNatural products with heteroaromatic
cores are ample and widespread in nature, with many compounds exhibiting
promising therapeutic properties. (+)-Armillariol C (1a) is a furan-based natural product isolated from Armillaria species. Herein, we report the first enantioselective
synthesis of (+)-armillariol C (1a, 79%
overall yield), its enantiomer (1b), and four other analogues,
on a gram-scale, using microwave-mediated, Suzuki–Miyaura cross-coupling
and Sharpless asymmetric dihydroxylation reactions. Compounds were
tested for plant- and mycelia-growth regulatory activity, with 1b, 7a, and 7b showing the strongest
inhibitory properties in a lettuce assay and 7b and 9b inhibiting Flammulina velutipes.
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heteroaromaticgram-scalecross-couplingmycelia-growthanalogueEvaluationspeciessynthesisenantioselectiveSuzukidihydroxylationenantiomerArmillariolSynthesiassaycoreNaturalnatureGram-ScalecompoundBiologicalSharplesmicrowave-mediatedvelutipeFlammulinaStereoselectiveHerein7 bfuran-basedarmillariolCompoundArmillaria
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