Synthesis 1988; 1988(4): 293-300
DOI: 10.1055/s-1988-27547
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Synthesis of New 3-(-2-Alkenyl)-2-hydroxy-5-methoxy-p-benzoquinones via Claisen Rearrangement of Original 5-Methoxy-4-(2-propenyloxy)-o-benzoquinones

Olivia Reinaud* , Patrice Capdevielle, Michel Maumy
  • *Laboratoire de Recherches Organiques de l'ESPCI associé au CNRS, 10 rue Vauquelin, F-75231 Paris Cedex 05, France
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Publication History

Publication Date:
20 August 2002 (online)

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 closely related to natural compounds. Thus, dihydroardisiaquinone A is synthesized in 5 steps from p-methoxyphenol.