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An improved approach to B-norsteroids: An one-pot preparation of 3β-acetoxy-5-oxo-5,6-seco-cholestan-6-oic and 3β-acetoxy-5,17-dioxo-5,6-seco-androstan-6-oic acids
A simple one-put procedure for the synthesis of the 5,6-seco-steroidal acids 9a,b in described in this paper. It consists of the epoxidation of the ▲ 5 -steroids, i.e., cholesteryl acetate (8a) and 17-oxo-aandrost-5-en-3β-yl acetate (8b) with peracetic acid (generated in situ by the H 2 WO 4 H 2 O 2 system), followed by the CrO 3 /H 2 SO_ oxidation of the thus formed epoxides. The 5,6-seco-steroidal acids 9a,b (obtained in about 90% and 77% yield, respectively) are transformed to the corresponding B-norsteroids by the known method (Beayer-Villiger oxidation and subsequent thermolysis of the respective β-lactones).
Source:
Journal of the Serbian Chemical Society, 1998, 63, 12, 955-959
TY - JOUR
AU - Stevović, Ljubomir S.
AU - Pavlović, Vladimir D.
AU - Martinović, Saša B.
AU - Dabović, Milan
AU - Juranić, Ivan
PY - 1998
UR - http://cer.ihtm.bg.ac.rs/handle/123456789/2706
AB - A simple one-put procedure for the synthesis of the 5,6-seco-steroidal acids 9a,b in described in this paper. It consists of the epoxidation of the ▲ 5 -steroids, i.e., cholesteryl acetate (8a) and 17-oxo-aandrost-5-en-3β-yl acetate (8b) with peracetic acid (generated in situ by the H 2 WO 4 H 2 O 2 system), followed by the CrO 3 /H 2 SO_ oxidation of the thus formed epoxides. The 5,6-seco-steroidal acids 9a,b (obtained in about 90% and 77% yield, respectively) are transformed to the corresponding B-norsteroids by the known method (Beayer-Villiger oxidation and subsequent thermolysis of the respective β-lactones).
PB - Serbian Chemical Society
T2 - Journal of the Serbian Chemical Society
T1 - An improved approach to B-norsteroids: An one-pot preparation of 3β-acetoxy-5-oxo-5,6-seco-cholestan-6-oic and 3β-acetoxy-5,17-dioxo-5,6-seco-androstan-6-oic acids
VL - 63
IS - 12
SP - 955
EP - 959
ER -
@article{
author = "Stevović, Ljubomir S. and Pavlović, Vladimir D. and Martinović, Saša B. and Dabović, Milan and Juranić, Ivan",
year = "1998",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/2706",
abstract = "A simple one-put procedure for the synthesis of the 5,6-seco-steroidal acids 9a,b in described in this paper. It consists of the epoxidation of the ▲ 5 -steroids, i.e., cholesteryl acetate (8a) and 17-oxo-aandrost-5-en-3β-yl acetate (8b) with peracetic acid (generated in situ by the H 2 WO 4 H 2 O 2 system), followed by the CrO 3 /H 2 SO_ oxidation of the thus formed epoxides. The 5,6-seco-steroidal acids 9a,b (obtained in about 90% and 77% yield, respectively) are transformed to the corresponding B-norsteroids by the known method (Beayer-Villiger oxidation and subsequent thermolysis of the respective β-lactones).",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "An improved approach to B-norsteroids: An one-pot preparation of 3β-acetoxy-5-oxo-5,6-seco-cholestan-6-oic and 3β-acetoxy-5,17-dioxo-5,6-seco-androstan-6-oic acids",
volume = "63",
number = "12",
pages = "955-959"
}
Stevović, L. S., Pavlović, V. D., Martinović, S. B., Dabović, M.,& Juranić, I. (1998). An improved approach to B-norsteroids: An one-pot preparation of 3β-acetoxy-5-oxo-5,6-seco-cholestan-6-oic and 3β-acetoxy-5,17-dioxo-5,6-seco-androstan-6-oic acids.
Journal of the Serbian Chemical Society
Serbian Chemical Society., 63(12), 955-959.
Stevović LS, Pavlović VD, Martinović SB, Dabović M, Juranić I. An improved approach to B-norsteroids: An one-pot preparation of 3β-acetoxy-5-oxo-5,6-seco-cholestan-6-oic and 3β-acetoxy-5,17-dioxo-5,6-seco-androstan-6-oic acids. Journal of the Serbian Chemical Society. 1998;63(12):955-959
Stevović Ljubomir S., Pavlović Vladimir D., Martinović Saša B., Dabović Milan, Juranić Ivan, "An improved approach to B-norsteroids: An one-pot preparation of 3β-acetoxy-5-oxo-5,6-seco-cholestan-6-oic and 3β-acetoxy-5,17-dioxo-5,6-seco-androstan-6-oic acids" Journal of the Serbian Chemical Society, 63, no. 12 (1998):955-959
