Functionalized 2-azabicyclo[3.3.1]nonanes. IV. synthesis of the indolo[3,2-f]morphan system. |
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Authors: | Josep Bonjoch Nuria Casamitjana Joan Bosch |
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Institution: | 1. Department of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Barcelona-28, Spain.;2. Department of Organic Chemistry, Faculty of Pharmacy, University of Valencia, Valencia-10, Spain. |
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Abstract: | A short route to the 2-azabicyclo3.3.1]nonan-7-one system is described. Condensation of 4-piperidones with diethyl 2-oxopropylphosphonate, followed by catalytic hydrogenation furnished the corresponding piperidylpropanones which were cyclized with mercuric acetate in acetic acid to the target target bicyclic ketones . The Fischer indole synthesis from afforded regioselectively the indole 3,2-f]morphan , a new heteromorphan type. |
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