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Synlett 1993; 1993(5): 333-334
DOI: 10.1055/s-1993-22444
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Synthesis and Diels-Alder Reaction of 4-Benzyl-1-tert -butyldimethylsiloxy-4H-furo[3,4-b]indole: Synthesis of Murrayaquinone-A

Yasuyoshi Miki* , Hiroko Hachiken
  • *Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-Osaka 577, Japan
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Publication Date:
19 March 2002 (online)

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4-Benzyl-1-tert-butyldimethylsiloxy-4H-furo[3,4-b] indole (2) was synthesized by selective reduction of 1-benzylindole-2,3-dicarboxylic anhydride with sodium borohydride, followed by treatment of the resulting lactone with base and tert-butyldimethylsilyl chloride. Diels-Alder reaction of the furoindole (2) with methyl acrylate and then treatment of the resulting adduct with boron trifluoride etherate gave methyl 9-benzyl-4-hydroxycarbazole-3-carboxylate in a regioselective manner, which was converted to murrayaquinone-A.