The enzymatic hydroxylation of steroidal β-diketones

✍ Scribed by Saul L. Neidleman; Patrick A. Diassi; Barbara Junta; Raymond K. Palmere; Paul Grabowich; Samuel C. Pan

• Book ID: 104223449
• Publisher: Elsevier Science
• Year: 1966
• Tongue: French
• Weight: 184 KB
• Volume: 7
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)90309-5

✦ Synopsis

The enzymatic hydroxylation of various aromatic compounds and proline have been reportedls3 using horseradish peroxidase. However, only one example of a steroidal hydroxylation, viz., the 108-hydroxylation of li'a-ethynyl-178-hydroxyestr-5(10)en-3-one using this enzyme system has been recorded4. We would like to report the facile hydroxylation of 16-ketoprogesterone (II)5 and 16-keto-A-norprogesterone (VI) by similar enzyme systems and by a non-enzymatic method. Both 16-ketoprogesterone (II) and 16-keto-A-norprogesterone (VI) were prepared by the Jones oxidation6 of 16a-hydroxyprogesterone' (I) and 16a-hydroxy-A-norprogesterone* (V) respectively. Like 115, 16-keto-A-norprogesterone, m.p. 128-130'; [a]i2-44' (chloroform) exists mainly in the enol form as evidenced by its ultraviolet absorption maxima at 233 and 286 W, infrared absorption bands at 1717, 1654 and 1625 crn.-l' and NMR spectrum which has a