Synthesis and molecular structure of 14,15-pyrrolidino-and 14,16-ethano derivatives of estrone.
Hydrolysis of 3-methoxy-16alpha-nitro-14,17-ethenoestra-1,3,5(10)-trien-17beta-yl acetate under weakly basic conditions leads to formation of 3-methoxy-2'-oxopyrrolidino-[4',5':14beta,15beta]-estra-1,3,5 (10)-trien-17-one, the structure of which has been confirmed by X-ray analysis and some chemical transformations. The reactivity of 3-methoxy-16alpha-nitro-14,17-ethanoestra-1,3,5(10)-trien-17beta-yl acetate under various conditions of basic hydrolysis has been investigated. The derived compounds have been identified by means of NMR spectroscopy and X-ray analysis.
Baranovsky
Alexander V
AV
Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str. 5/2, 220143 Minsk, Belarus. baranovsky@iboch.bas-net.by
Bolibrukh
Dmitry A
DA
Bull
James R
JR
Lyakhov
Alexander S
AS
Khripach
Vladimir A
VA
D004970:Estrone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D011759:Pyrrolidines; D004970:Estrone