52077-56-2Relevant articles and documents
Synthesis of Cortoic Acid 3-Glucuronides
Hosoda, Hiroshi,Yokohama, Hiromitsu,Nambara, Toshio
, p. 1359 - 1364 (2007/10/02)
The synthesis of the 3-glucuronides of cortoic acids, metabolites of cortisol, is described. 20α-Cortolonic acid 3-glucuronide (11) and its 20β-epimer (12) were prepared starting from tetrahydrocortisone (1).The cortolonic acid 20-acetate methyl esters (7,8) were the key intermediates.The 20-oxo-21-aldehyde (2) obtained from 1 by oxidation with cupric acetate was derivatized into 20-epimeric methyl cortolonates (3).When 3 was treated with tert-butyldimethylsilyl chloride and imidazole in dimethylformamide-pyridine, selective silylation of the hydroxyl group at C-3 took place.Subsequent acetylation with acetic anhydride in pyridine gave the separable 20-acetates (5,6), which, on removal of the silyl group at C-3 with sulfuric acid, were converted into the desired intermediates.Introduction of the glucuronyl residue into the C-3 position was carried out by means of the Koenigs-Knorr reaction.The cortolic acid 3-glucuronides (21, 22) were synthesized from 5β-dihydrocortisol (13).Keywords - cortisol metabolite; cortoic acid; cortolic acid 3-glucuronide; cortolonic acid 3-glucuronide; Koenigs-Knorr reaction.
