Tetrapropylammonium perruthenate as a mild and efficient oxidant for sensitive steroidal alcohols.
Tetrapropylammonium perruthenate N-methylmorpholine N-oxide oxidation of steroidal alcohols is described. The reagent combination is mild and gave good yields of the corresponding ketones. Although the oxidation can generate ketones from 3-, 11-, 15-, 17-, and 20-hydroxy steroids, the oxidation of homoallylic alcohols proceeds in low yields. Finally, we observed that the oxidation reagents will convert 17 alpha-hydroxy-20-keto steroids to 17-keto systems in excellent yield.
Acosta
C K
CK
Department of Organic Chemistry, Southwest Foundation for Biomedical Research, San Antonio, Texas 78228-0147.
Rao
P N
PN
Kim
H K
HK
D006907:17-alpha-Hydroxypregnenolone / Q000378:metabolism; D019326:17-alpha-Hydroxyprogesterone; D000438:Alcohols / Q000378:metabolism*; D000735:Androstenedione / Q000378:metabolism; D003497:Cyclic N-Oxides / Q000494:pharmacology*; D003687:Dehydroepiandrosterone / Q000031:analogs & derivatives / Q000378:metabolism; D019314:Dehydroepiandrosterone Sulfate; D006908:Hydroxyprogesterones / Q000378:metabolism; D007659:Ketones / Q000378:metabolism; D009025:Morpholines / Q000494:pharmacology*; D009942:Organometallic Compounds / Q000494:pharmacology; D016877:Oxidants / Q000494:pharmacology*; D010084:Oxidation-Reduction; D011282:Pregnenediones / Q000378:metabolism; D011284:Pregnenolone / Q000378:metabolism; D000644:Quaternary Ammonium Compounds / Q000494:pharmacology; D012428:Ruthenium / Q000494:pharmacology; D013256:Steroids / Q000378:metabolism*
D000438:Alcohols; D003497:Cyclic N-Oxides; D006908:Hydroxyprogesterones; D007659:Ketones; D009025:Morpholines; D009942:Organometallic Compounds; D016877:Oxidants; D011282:Pregnenediones; D000644:Quaternary Ammonium Compounds; D013256:Steroids; C082683:tetrapropylammonium perruthenate; D006907:17-alpha-Hydroxypregnenolone; D000735:Androstenedione; D003687:Dehydroepiandrosterone; D019314:Dehydroepiandrosterone Sulfate; D019326:17-alpha-Hydroxyprogesterone; D011284:Pregnenolone; D012428:Ruthenium; C067960:4-methylmorpholine N-oxide