Synthesis and biological activity of 17-chloro-16(17) unsaturated D-homo antiprogestins.
An efficient approach to 17-chloro-16(17) unsaturated D-homo antiprogestins is described. The key steps of the synthesis are a ring-expansion via dichlorocarbene addition to a 17-silyl enol ether and a palladium catalyzed coupling of an 11 beta-(4-aryltriflate) with tributyl(1-ethoxyethenyl)stannane or diethyl(3-pyridinyl)-borane. The new progesterone antagonists were tested for their biological activities and compared to those of known antiprogestins.
Schwede
W
W
Research Laboratories of Schering AG, Berlin, Germany.
Cleve
A
A
Neef
G
G
Ottow
E
E
Stöckemann
K
K
Wiechert
R
R
D000028:Abortion, Induced / Q000379:methods; D000818:Animals; D005260:Female; D015394:Molecular Structure; D011247:Pregnancy; D011372:Progestins / Q000037:antagonists & inhibitors*; D051381:Rats; D013258:Steroids, Chlorinated / Q000138:chemical synthesis* / Q000494:pharmacology*
D011372:Progestins; D013258:Steroids, Chlorinated