Process improvements in steroid chemistry

Steroids containing a cyclohexene moiety are efficiently oxidized to the corresponding alpha,beta-unsaturated ketone using copper iodide and t-butyl hydroperoxide. A steroid compound containing the alpha,beta-unsaturated ketone structure is efficiently converted to the corresponding vicinal diol usi...

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Main Authors BURGOYNE DAVID L, KELLEHER EUGENE W, PASCHALIDES NICHOLAS D, SHEN YAPING, RAMACHANDRAN KISHORE, ZHOU YUANLIN, JI GUEIJUN
Format Patent
LanguageEnglish
Published 03.01.2006
Subjects
APPARATUS THEREFOR
CHEMISTRY
GENERAL METHODS OF ORGANIC CHEMISTRY
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
STEROIDS
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Abstract Steroids containing a cyclohexene moiety are efficiently oxidized to the corresponding alpha,beta-unsaturated ketone using copper iodide and t-butyl hydroperoxide. A steroid compound containing the alpha,beta-unsaturated ketone structure is efficiently converted to the corresponding vicinal diol using a hydroborating reagent followed by oxidative workup, e.g., borane followed by sodium perborate. Benzoyl and substituted benzoyls are superior protecting groups for hydroxyl groups present in the compounds.
AbstractList Steroids containing a cyclohexene moiety are efficiently oxidized to the corresponding alpha,beta-unsaturated ketone using copper iodide and t-butyl hydroperoxide. A steroid compound containing the alpha,beta-unsaturated ketone structure is efficiently converted to the corresponding vicinal diol using a hydroborating reagent followed by oxidative workup, e.g., borane followed by sodium perborate. Benzoyl and substituted benzoyls are superior protecting groups for hydroxyl groups present in the compounds.
Author ZHOU YUANLIN
RAMACHANDRAN KISHORE
SHEN YAPING
JI GUEIJUN
KELLEHER EUGENE W
BURGOYNE DAVID L
PASCHALIDES NICHOLAS D
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– fullname: SHEN YAPING
– fullname: RAMACHANDRAN KISHORE
– fullname: ZHOU YUANLIN
– fullname: JI GUEIJUN
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Snippet Steroids containing a cyclohexene moiety are efficiently oxidized to the corresponding alpha,beta-unsaturated ketone using copper iodide and t-butyl...
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SubjectTerms APPARATUS THEREFOR
CHEMISTRY
GENERAL METHODS OF ORGANIC CHEMISTRY
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
STEROIDS
Title Process improvements in steroid chemistry
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