A tandem cross-coupling/S(N)Ar approach to functionalized carbazoles.
A novel route to functionalized carbazoles utilizing a tandem Suzuki cross-coupling/SNAr protocol is described. This process was found to be compatible with a variety of electron-withdrawing groups including aldehydes, esters, and sulfones. Using this method, a concise total synthesis (four steps, 50% overall yield) of the carbazole alkaloid glycosinine was achieved.
St Jean
David J
DJ
Department of Medicinal Chemistry, Amgen Inc., One Amgen Center Drive, Thousand Oaks, CA 91320-1799, USA. david.st.jean@amgen.com
Poon
Steve F
SF
Schwarzbach
Jamie L
JL
D001128:Argon / Q000737:chemistry*; D002227:Carbazoles / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013455:Sulfur / Q000737:chemistry*
D002227:Carbazoles; D003432:Cross-Linking Reagents; C041514:carbazole; D001128:Argon; D013455:Sulfur