3329-79-1Relevant articles and documents
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Heusler et al.
, p. 1586,1597 (1959)
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Aldosterone Glucuronide, an Important Biomarker: Synthesis and Structure Elucidation of Novel Isomers
Guha, Somraj,Senthilkumar, Soundararasu,Tietze, Lutz F.,Vo?, Edgar
supporting information, p. 15733 - 15737 (2020/11/30)
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.
18,21-ANHYDROALDOSTERONE AND DERIVATIVES
Harnik, M.,Kashman, Y.,Cojocaru, M.,Lewicka, S.,Vecsei, P.
, p. 11 - 20 (2007/10/02)
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.
