THE REDUCTION OF STEROID 2-ALPHA-FLUORO 4-EN-3-ONES

Reduction of testosterone with potassium tri-(R,S)-sec-butylborohydride gives predominantly the allylic 3.beta.-alcohol, while 2.alpha.-fluorotestosterone is converted solely to 2.alpha.-fluoro-4-androstene-3.alpha.,17.beta.-diol, and 2.alpha.-fluoro-4-androstene-3,17-dione to 2.alpha.-fluoro-3.alph...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 53; no. 13; pp. 3057 - 3059
Main Authors GONDOS, G, MCGIRR, LG, JABLONSKI, CR, SNEDDEN, W, ORR, JC
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 24.06.1988
American Chemical Society
Subjects
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Steroids
Steroid
Silicon Organic compounds
Diketone
Dehydrogenase
Organosilicon hydride
Allylic compound
Chemical reduction
Stereoselectivity
Testosterone
Tertiary alcohol
Boron Organic compounds
Enone
Enzymatic reaction
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Summary:Reduction of testosterone with potassium tri-(R,S)-sec-butylborohydride gives predominantly the allylic 3.beta.-alcohol, while 2.alpha.-fluorotestosterone is converted solely to 2.alpha.-fluoro-4-androstene-3.alpha.,17.beta.-diol, and 2.alpha.-fluoro-4-androstene-3,17-dione to 2.alpha.-fluoro-3.alpha.-hydroxy-4-androsten-17-one. Reduction of testosterone with (R,R)- or (S,S)-Rh-DIOP and dihydrosilanes give predominantly allylic alcohols, while with the same catalysts and monohydrosilanes no allylic alcohols are found, the 4-double bond being instead reduced. The chirality of the DIOP reagents contributes only to a minor extent to stereoselectivity of 3-ketone reduction.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00248a028