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Synthesis 1987; 1987(2): 181-183
DOI: 10.1055/s-1987-27882
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A Simple Synthesis of Steroidal 3α,5-Cyclo-6-ones and their Efficient Transformation to Steroidal 2-En-6-ones

Masakazu Aburatani* , Tadashi Takeuchi, Kenji Mori
  • *Research Division, Fuji Chemical Industries, Ltd., 530, Chokeiji, Takaoka, Toyama 933, Japan
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Publication Date:
12 September 2002 (online)

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Sterols 1 were converted to 3α-5-cyclo-6-ones 4 via their mesylates and subsequent oxidation. Refluxing 4 with sodium bromide/p-toluene sulfonic acid in dimethylformamide gave steroidal 2-en-6-ones 5, among which 5d is an important brassinolide intermediate.