A novel, highly efficient route to the key steganone intermediate 2,3,4-trimethoxy-6,7-methylenedioxy-9-(pyrrolidin-1-yl)phenanthrene (8) is described. Resolution of the derived 5,6,7,8-tetrahydro-1,2,3-trimethoxy-10,11-methylenedioxy-8-oxodibenzo[a,c]cyclo-octene-6-carboxylic acid and further elaboration of the relevant enantiomer (11) leads to the first synthesis of enantiomerically pure (–)-steganone (1).
E. R. Larson and R. A. Raphael, J. Chem. Soc., Perkin Trans. 1, 1982, 521 DOI: 10.1039/P19820000521
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