21551-67-7Relevant articles and documents
Naturally occurring 5-lipoxygenase inhibitors. VI. Structures of ardisiaquinones D, E, and F from Ardisia sieboldii
Fukuyama,Kiriyama,Kodama,Iwaki,Hosozawa,Aki,Matsui
, p. 1391 - 1394 (2007/10/02)
New 1,4-benzoquinone derivatives, ardisiaquinones D (2), E (4), and F (5) along with the known ardisiaquinones A (1) and B (3) have been isolated from the leaves of Ardisia sieboldii (Myrsinaceae) and shown to be 5-lipoxygenase inhibitors. Their structure
Synthesis of New 3-(-2-Alkenyl)-2-hydroxy-5-methoxy-p-benzoquinones via Claisen Rearrangement of Original 5-Methoxy-4-(2-propenyloxy)-o-benzoquinones
Reinaud, Olivia,Capdevielle, Patrice,Maumy, Michel
, p. 293 - 300 (2007/10/02)
The Claisen rearrangement is extended to compounds containing the benzoquinone moiety, obtained by regioselective nucleophilic substitution on 4-(p-methoxyphenoxy)-5-methoxy-o-benzoquinone (1).In the most general case, 5-methoxy-4-(2-propenyloxy)-o-benzoquinones 3 rearrange quantitatively into (E)-3-(2-alkenyl-2-hydroxy-5-methoxy-p-benzoquinones 4.Furfuryl or (2-thienyl)methyl ethers isomerize to 3-(2-methyl-3-furyl)- and 3-(2-methyl-3-thienyl)-2-hydroxy-5-methoxy-p-benzoquinones.This new synthetic method provides an efficient route to new hydroxybenzoquinones closelyrelated to natural compounds.Thus, dihydroardisiaquinone A is synthesized in 5 steps from p-methoxyphenol.