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Synthesis 1990; 1990(9): 822-824
DOI: 10.1055/s-1990-27026
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Regio- and Stereospecific Total Synthesis of a Racemic A,19-Dinorsteroid

Wei-shan Zhou* , Guo-ping Wei
  • *Shanghai Institute of Organic Chemistry, Academia Sinica, 345 Lingling Lu Shanghai 200032, People's Republic of China
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Publication Date:
17 September 2002 (online)

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DL-A-nor-estr-3(5)-ene-2,17-dione is regio- and stereospecifically synthesized from 1-acetal-protected 7a-methyl-2,3,5,6,7,7a-hexa- hydroindene-1,5-dione in five steps in ca. 23% overall yield. The key step is the regiospecific trapping of an enolate of the dione with 6,6-(1,2-ethanediyldioxy)-2-trimethylsilyl-3-oxo-1-heptene.