Reduction of 1,4-dien-3-one steroids with LiAl2H4 or NaB2H4: stereospecific deuterium-labeling at the c-1alpha position of a 4-en-3-one steroid.
Reduction of a double bond at C-1 of 1,4-dien-3-one steroids 7 and 8 with LiAl2H4 in THF or NaB2H4 in MeOH and H2O gave stereospecifically [1alpha-2H]-labeled 4-en-3-one steroids 9 and 10, respectively. When the deuterated solvents, MeO2H and 2H2O, were used for the reaction of steroid 8 with NaB2H4, [1alpha,2xi-2H2]-labeled compound 10 was produced. This indicates that the reaction proceeds through the initial hydride attack at the C-1alpha position, followed by ketonization of the 2-en-3-ol intermediate.
Numazawa
Mitsuteru
M
Tohoku Pharmaceutical University, Sendai, Japan. numazawa@tohoku-pharm.ac.jp
Handa
Wakako
W
D017607:Aluminum Compounds / Q000737:chemistry*; D001894:Borohydrides / Q000737:chemistry*; D003903:Deuterium / Q000737:chemistry*; D007553:Isotope Labeling; D007659:Ketones / Q000737:chemistry; D018020:Lithium Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000737:chemistry; D008956:Models, Chemical; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry*; D013739:Testosterone / Q000031:analogs & derivatives; D014867:Water / Q000737:chemistry
D017607:Aluminum Compounds; D001894:Borohydrides; D007659:Ketones; D018020:Lithium Compounds; D013256:Steroids; D014867:Water; D013739:Testosterone; C042073:lithium aluminum hydride; C025364:sodium borohydride; D003903:Deuterium; D000432:Methanol