Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 18, Pages 6878-6884Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo071137b
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Upon treatment with 30 mol % of Co-2(CO)(8) and 30 mol % of TMTU in toluene at 70 degrees C, benzene-bridged alkynecarbodiimides efficiently underwent a ring-closing reaction to give the pyrrolo[2,3-b]indol-2-ones in good yields. These conditions could nearly suppress the formation of the urea derivatives, which were consistently observed when 10 mol % of Co-2(CO)(8) and 60 mol % of TMTU in benzene were used. The synthesis of the eight hexahydropyrrolo[2,3-b]indole alkaloids was accomplished from the resulting pyrrolo[2,3-b]indol-2-ones via the introduction of an angular substituent at the C-3a-position by treatment with NaBH4/alkyl bromide as the crucial step.
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