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The effect of C-2 substitution on the stereoselective reduction of steroid C-3 ketones with lithium tris-(R,S-1,2-dimethylpropyl)-borohydride and sodium borohydride was investigated. The C-2 mono- and di-substituted chloro and methyl derivatives were predominantly reduced to one of the epimeric alcohols. The 2 alpha-chloro and 2 alpha-methyl derivatives of 17 beta-acetoxy-5 alpha-androstan-3-one undergo stereoselective reduction with lithium tris-(R,S-1,2-dimethylpropyl)-borohydride to the axial (3 alpha) alcohol as observed in the unsubstituted compound, whereas sodium borohydride gives predominantly the equatorial (3 beta) alcohol. The 2 beta-chloro, 2 beta-methyl, 2,2-dichloro, and 2,2-dimethyl derivatives are reduced predominantly to the equatorial (3 beta) alcohol by both reagents.
J F Templeton, and
V P Kumar, and
R K Gupta, and
A M Friesen
January 1968,
Journal of the American Chemical Society,
J F Templeton, and
V P Kumar, and
R K Gupta, and
A M Friesen
May 1967,
Tetrahedron letters,
J F Templeton, and
V P Kumar, and
R K Gupta, and
A M Friesen
January 1974,
Il Farmaco; edizione scientifica,
J F Templeton, and
V P Kumar, and
R K Gupta, and
A M Friesen
March 2024,
Organic & biomolecular chemistry,
J F Templeton, and
V P Kumar, and
R K Gupta, and
A M Friesen
January 1973,
Biochimica et biophysica acta,
J F Templeton, and
V P Kumar, and
R K Gupta, and
A M Friesen
October 2010,
Steroids,
J F Templeton, and
V P Kumar, and
R K Gupta, and
A M Friesen
January 1969,
Journal of the Chemical Society. Perkin transactions 1,
J F Templeton, and
V P Kumar, and
R K Gupta, and
A M Friesen
November 2008,
The Journal of organic chemistry,
J F Templeton, and
V P Kumar, and
R K Gupta, and
A M Friesen
May 2012,
Organic & biomolecular chemistry,
J F Templeton, and
V P Kumar, and
R K Gupta, and
A M Friesen
January 1961,
Transactions of the Kansas Academy of Science. Kansas Academy of Science,
