18,21-Anhydroaldosterone and derivatives.
18,21-Anhydroaldosterone 8, 18,21-anhydro-19-noraldosterone 9, and 3 alpha, 5 beta-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
M
Department of Biotechnology, Tel-Aviv University, Israel.
Kashman
Y
Y
Cojocaru
M
M
Lewicka
S
S
Vecsei
P
P
D000450:Aldosterone / Q000031:analogs & derivatives*; D055598:Chemical Phenomena; D002621:Chemistry; D013055:Spectrophotometry, Infrared
D000450:Aldosterone; C061690:18,21-anhydroaldosterone