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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

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1998
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Authors
Stevović, Ljubomir S.
Pavlović, Vladimir D.
Martinović, Saša B.
Dabović, Milan
Juranić, Ivan
Article (Published version)
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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).
Source:
Journal of the Serbian Chemical Society, 1998, 63, 12, 955-959
Publisher:
  • Serbian Chemical Society

ISSN: 0352-5139

Scopus: 2-s2.0-0000199303
[ Google Scholar ]
4
URI
http://cer.ihtm.bg.ac.rs/handle/123456789/2706
Collections
  • Radovi istraživača / Researchers' publications
Institution
IHTM
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 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, 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 SocietySerbian Chemical Society., 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" 63, no. 12 (1998):955-959

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