Issue 12, 2002

A new entry to 9-azabicyclo[3.3.1]nonanes using radical translocation/cyclisation reactions of 2-(but-3-ynyl)-1-(o-iodobenzoyl)piperidines

Abstract

The 2-[4-(trimethylsilyl)but-3-ynyl]piperidines 16a–c, upon treatment with tributyltin hydride in the presence of azoisobutyronitrile in refluxing toluene, gave the 9-azabicyclo[3.3.1]nonanes 17a–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.

Graphical abstract: A new entry to 9-azabicyclo[3.3.1]nonanes using radical translocation/cyclisation reactions of 2-(but-3-ynyl)-1-(o-iodobenzoyl)piperidines

Supplementary files

Article information

Article type
Paper
Submitted
02 Apr 2002
Accepted
22 Apr 2002
First published
13 May 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1438-1443

A new entry to 9-azabicyclo[3.3.1]nonanes using radical translocation/cyclisation reactions of 2-(but-3-ynyl)-1-(o-iodobenzoyl)piperidines

T. Sato, T. Yamazaki, Y. Nakanishi, J. Uenishi and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 2002, 1438 DOI: 10.1039/B203243K

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