A new entry to 9-azabicyclo[3.3.1]nonanes using radical translocation/cyclisation reactions of 2-(but-3-ynyl)-1-(o-iodobenzoyl)piperidinesElectronic supplementary information (ESI) available: Experimental details for 5–16. See http://www.rsc.org/suppdata/p1/b2/b203243k/
Sato, Tatsunori; Yamazaki, Taro; Nakanishi, Yumi; Uenishi, Jun-ichi; Ikeda, Masazumi; Sato Tatsunori; Kyoto Pharmaceutical University, Misasagi; Yamazaki Taro; Kyoto Pharmaceutical University, Misasagi; Nakanishi Yumi; Kyoto Pharmaceutical University, Misasagi; Uenishi Jun-ichi; Kyoto Pharmaceutical University, Misasagi; Ikeda Masazumi; Kyoto Pharmaceutical University, Misasagi
Журнал:
Journal of the Chemical Society, Perkin Transactions 1
Дата:
2002
Аннотация:
The 2-[4-(trimethylsilyl)but-3-ynyl]piperidines 16aâ c, upon treatment with tributyltin hydride in the presence of azoisobutyronitrile in refluxing toluene, gave the 9-azabicyclo[3.3.1]nonanes 17aâ c in high yields, respectively. Compound 17c was subjected to desilylation, ozonolysis, and subsequent 1,2-transposition of the resulting carbonyl group to give 9-benzoyl-1-methyl-9-azabicyclo[3.3.1]nonan-3-one, a potential precursor for the synthesis of (±)-euphococcinine.
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