Synthesis p. 293 - 300 (1988)
Update date:2022-08-05
Topics:
Reinaud, Olivia
Capdevielle, Patrice
Maumy, Michel
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.
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Doi:10.1021/jo00254a054
(1988)Doi:10.1016/S0040-4039(00)97606-8
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