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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Stevović, Ljubomir S.Pavlović, Vladimir D.
Martinović, Saša B.
Dabović, Milan
Juranić, Ivan

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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).
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Journal of the Serbian Chemical Society, 1998, 63, 12, 955-959Publisher:
- Serbian Chemical Society
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IHTMTY - JOUR AU - Stevović, Ljubomir S. AU - Pavlović, Vladimir D. AU - Martinović, Saša B. AU - Dabović, Milan AU - Juranić, Ivan PY - 1998 UR - https://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 UR - https://hdl.handle.net/21.15107/rcub_cer_2706 ER -
@article{ author = "Stevović, Ljubomir S. and Pavlović, Vladimir D. and Martinović, Saša B. and Dabović, Milan and Juranić, Ivan", year = "1998", 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", url = "https://hdl.handle.net/21.15107/rcub_cer_2706" }
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. in Journal of the Serbian Chemical Society Serbian Chemical Society., 63(12), 955-959. https://hdl.handle.net/21.15107/rcub_cer_2706
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. in Journal of the Serbian Chemical Society. 1998;63(12):955-959. https://hdl.handle.net/21.15107/rcub_cer_2706 .
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" in Journal of the Serbian Chemical Society, 63, no. 12 (1998):955-959, https://hdl.handle.net/21.15107/rcub_cer_2706 .