A convenient, 40% overall yield synthesis of 2,3,17β-triacetoxy-1,3,5(10)-estratriene is described, which involves epoxidation of 19-nortestosterone and subsequent acetylation, lead tetra-acetate acetoxylation of the so-formed 17β-acetoxy-4β,5-epoxy-5β-estran-3-one, and aromatization of ring A, by means of acidic alumina, of the resulting 2α and 2β epimers of 2,17β-diacetoxy-4β,5-epoxy-5β-estran-3-one.
Keywords:
aromatization of ring / acetylation / acidic alumina
TY - JOUR
AU - Mihalilović, M.Lj.
AU - Foršek, Jože
AU - Lorenc, Ljubinka B.
PY - 1977
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4581
AB - A convenient, 40% overall yield synthesis of 2,3,17β-triacetoxy-1,3,5(10)-estratriene is described, which involves epoxidation of 19-nortestosterone and subsequent acetylation, lead tetra-acetate acetoxylation of the so-formed 17β-acetoxy-4β,5-epoxy-5β-estran-3-one, and aromatization of ring A, by means of acidic alumina, of the resulting 2α and 2β epimers of 2,17β-diacetoxy-4β,5-epoxy-5β-estran-3-one.
PB - Elsevier
T2 - Tetrahedron
T1 - A novel procedure for the aromatization of ring a in 19-nortestosterone
VL - 33
IS - 2
SP - 235
EP - 237
DO - 10.1016/0040-4020(77)80132-4
ER -
@article{
author = "Mihalilović, M.Lj. and Foršek, Jože and Lorenc, Ljubinka B.",
year = "1977",
url = "https://cer.ihtm.bg.ac.rs/handle/123456789/4581",
abstract = "A convenient, 40% overall yield synthesis of 2,3,17β-triacetoxy-1,3,5(10)-estratriene is described, which involves epoxidation of 19-nortestosterone and subsequent acetylation, lead tetra-acetate acetoxylation of the so-formed 17β-acetoxy-4β,5-epoxy-5β-estran-3-one, and aromatization of ring A, by means of acidic alumina, of the resulting 2α and 2β epimers of 2,17β-diacetoxy-4β,5-epoxy-5β-estran-3-one.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "A novel procedure for the aromatization of ring a in 19-nortestosterone",
volume = "33",
number = "2",
pages = "235-237",
doi = "10.1016/0040-4020(77)80132-4"
}
Mihalilović, M.Lj., Foršek, J.,& Lorenc, L. B. (1977). A novel procedure for the aromatization of ring a in 19-nortestosterone.
Tetrahedron
Elsevier., 33(2), 235-237.
https://doi.org/10.1016/0040-4020(77)80132-4
Mihalilović M, Foršek J, Lorenc LB. A novel procedure for the aromatization of ring a in 19-nortestosterone. Tetrahedron. 1977;33(2):235-237
Mihalilović M.Lj., Foršek Jože, Lorenc Ljubinka B., "A novel procedure for the aromatization of ring a in 19-nortestosterone" Tetrahedron, 33, no. 2 (1977):235-237,
https://doi.org/10.1016/0040-4020(77)80132-4 .
