Photochemistry of 3ζ,5ζ-epoxycholestan-6-ones

Foster, Richard W.; Marples, B. A.

doi:10.1039/p19890000579

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Other Reactions Of Olefinic and Aromatic Steroids1

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1989

1993

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“…Nucleophilic displacement of bromine from 2-bromooestradiol (121) occurs with sodium methoxide in the presence of copper(r) iodide and benzo-15-crown-5-, 15-crown-5, dibenzo-18-crown-6, or 18-cr0wn-6.~~ Thus, 2-methoxyoestradiol (122) is obtained in 84% yield when the bromide (121) is stirred with sodium methoxide, copper(1) iodide, and benzo-15-crown-5 in dimethylformamide at 105-1 10 "C. Oxygenation of dibromo-oestradiol (123) with nitric acid in acetic acid gives the dienone (124), which is reduced to the ketol(l25) by hydrogenation over palladium. 64 The ketol(l25) is converted into the 4-en-3-one (126) with perchloric acid, toluene-psulfonic acid, or Nafion-H. The corresponding 17-0x0-and 1601,17/3-dihydroxy-19-norsteroids can also be prepared by this sequence of reactions.…”

Section: Other Reactions Of Olefinic and Aromatic Steroidsmentioning

confidence: 99%