Convenient synthesis of 18-hydroxylated cortisol and prednisolone.
18,20-Epoxy-11 beta,17 alpha,20 beta,21-tetrahydroxypregn-4-en-3-one was synthesized by the application of hypoiodite reaction to the cortisol acetonide. The intermediary 18-iodo derivative was converted to the 11-oxo steroid by chromic acid prior to silver ion-assisted solvolysis. Removal of the protective group with hydrochloric acid was finally carried out to give the desired 11 beta,17 alpha,18,21-tetrahydroxypregn-4-ene-3,20-dione as the hemiacetal form. 18,20-Epoxy-11 beta-17 alpha,20 beta,21- tetrahydroxypregna-1,4-dien-3-one was also prepared from prednisolone through a similar reaction sequence.
Kurosawa
T
T
Faculty of Pharmaceutical Sciences, Higashi-Nippon-Gakuen University, Hokkaido, Japan.
Ikegawa
S
S
Chiba
H
H
Ito
Y
Y
Nakagawa
S
S
Kobayashi
K
K
Tohma
M
M
D006854:Hydrocortisone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007454:Iodides; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011239:Prednisolone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D012834:Silver; D018030:Silver Compounds
C078536:18-hydroxyprednisolone; D007454:Iodides; D018030:Silver Compounds; D012834:Silver; C030584:silver iodide; D011239:Prednisolone; C033689:18-hydroxycortisol; D006854:Hydrocortisone