- Aldosterone Glucuronide, an Important Biomarker: Synthesis and Structure Elucidation of Novel Isomers
-
Aldosterone 1 is a mineralocorticoid, it has great influence on the blood pressure and its glucuronide is an important marker for the detection of several diseases. Here, we describe the chemical synthesis of different aldosterone-18- and 20-glucuronides. Reaction of trimethylsilyl 2,3,4-tri- acetyl-1-β-glucuronic acid methyl ester 5 b and aldosterone diacetate 11 in the presence of TMSOTf gave the 18-α-glucuronide 9 a. The 18-β-glucuronide 15 b and the 20-β-glucuronide 16 b could be obtained by reaction of methyl 2,3,4-tri-O-isobutyryl-1α-glucuronate trichloroacetimidate 14 and aldosterone 21-acetate 8 in the presence of TMSOTf or BF3?OEt2. Finally, reaction of aldosterone 21-acetate 8 and methyl 2,3,4-triacetyl-1α-glucuronate trichloroacetimidate 19 in the presence of TMSOTf gave the corresponding methyl 18-β-triacetylglucuronate 9 b, which was transformed into the desired aldosterone-18-β-glucuronide 3 by two enzyma- tic transformations.
- Guha, Somraj,Senthilkumar, Soundararasu,Tietze, Lutz F.,Vo?, Edgar
-
supporting information
p. 15733 - 15737
(2020/11/30)
-
- 18-Substituted Steroids. Part 16. Synthesis of 6β-Hydroxy- and 6α-Hydroxy-aldosterone and their 17α-Isomers
-
Aldosterone has been converted via its 3-enol 3,18,21-triacetate into 6β-hydroxyaldosterone and 6α-hydroxyaldosterone, which are slowly transformed in dilute alkaline solution into their 17α-isomers. 6β-Hydroxyaldosterone and 6β-hydroxy-17-isoaldosterone were identical with products isolated from liver microsomal incubations of aldosterone.
- Kirk, David N.,Miller, Barry W.,Cooley, George,Latif, Syed A.,Morris, David J.
-
p. 1274 - 1289
(2007/10/02)
-
- 18,21-ANHYDROALDOSTERONE AND DERIVATIVES
-
18,21-Anhydroaldosterone 8, 18,21-anhydro-19-noraldosterone 9, and 3α,5β-tetrahydro-18,21-anhydro-19-noraldosterone 13, which may be present in acid-processed urine, were prepared by cleaving their 20-ketal derivatives 2, 3, and 12 with hot mineral acid.Compounds 8 and 9 were also made by direct dehydration of aldosterone 5 and 19-noraldosterone 10 in good yield.The reverse ring opening of 8 to 5 could be carried out in moderate yield with an acetic acid-acetic anhydride-perchloric acid mixture, while an analogous ring opening of 9 gave only a poor yield of 10.
- Harnik, M.,Kashman, Y.,Cojocaru, M.,Lewicka, S.,Vecsei, P.
-
-