Abstract:
:A partial synthesis of the title compound, 4'-(dimethylamino)-17 beta-hydroxy-17 alpha-(1-propynyl)benzo[12,12a]-11 alpha,18-cyclo-12a,12b- dihomo-13 alpha-estr-4-en-3-one 1, is reported. The key step in this synthesis represents an intramolecular alkenylaryl radical cyclization. Treatment of 18-[bromo-5-(dimethylamino)phenyl]gona-5,9(11)-diene-3,17-dione-3, 17- bis[cyclic 1,2-ethanediyl acetal] 5 with tributyl tin hydride and a radical initiator introduces the desired 11 beta,18-bridge. The reduced progesterone receptor affinity of this RU 38 486 analog contributes valuable information to the empirical characterization of the steroid binding site of the receptor protein and explains the observed lack of in vivo antigestational activity.
journal_name
Steroidsjournal_title
Steroidsauthors
Ottow E,Beier S,Elger W,Fritzemeier KH,Neef G,Wiechert Rdoi
10.1016/0039-128x(94)90026-4subject
Has Abstractpub_date
1994-03-01 00:00:00pages
185-9issue
3eissn
0039-128Xissn
1878-5867pii
0039-128X(94)90026-4journal_volume
59pub_type
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