Gram-Scale, Stereoselective Synthesis and Biological
Evaluation of (+)-Armillariol C
Version 3 2018-02-09, 21:43
Version 2 2017-10-17, 15:49
Version 1 2017-08-21, 17:39
Posted on 2018-02-09 - 21:43
Natural 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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Reddy, M. Damoder; Kobori, Hajime; Mori, Takumi; Wu, Jing; Kawagishi, Hirokazu; Watkins, E. Blake (2017). Gram-Scale, Stereoselective Synthesis and Biological
Evaluation of (+)-Armillariol C. ACS Publications. Collection. https://doi.org/10.1021/acs.jnatprod.7b00484
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AUTHORS (6)
MR
M. Damoder Reddy
HK
Hajime Kobori
TM
Takumi Mori
JW
Jing Wu
HK
Hirokazu Kawagishi
EW
E. Blake Watkins
KEYWORDS
heteroaromaticgram-scalecross-couplingmycelia-growthanalogueEvaluationspeciessynthesisenantioselectiveSuzukidihydroxylationenantiomerArmillariolSynthesiassaycoreNaturalnatureGram-ScalecompoundBiologicalSharplesmicrowave-mediatedvelutipeFlammulinaStereoselectiveHerein7 bfuran-basedarmillariolCompoundArmillaria