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Report | Regular issue | Vol 20, No. 6, 1983, pp.1077-1081
Published online, 1st January, 1970
DOI: 10.3987/R-1983-06-1077
A Short and Efficient Synthesis of C-Nor-dihydrocodeinone — The Antipode of Goto’s Sinomenilone

Michael Bös, Wilhelm Fleischhacker, and Peter Tschany

*Institute of Pharmaceutical Chemistry, University of Vienna, Währinger Strasse 10, A-1090 Vienna, Austria

Abstract

In a four step synthesis, when using dihydrocodeinone, the C-nor-derivative 2 will be obtained in good yields. The reduction of the ringsize is achieved by bromination to the 1,7,7-tribromoketone 4 and heating it in an alkaline solution. Decarbonylation of the α-hydroxy acid 5 and subsequent catalytic hydrogenation of 6 lead to the desired enantiomer of Goto’s sinomenilone.