Lokman Torun

TUBITAK MAM Chemistry Institute, P K 21 Gebze, Kocaeli 41470, Turkey

Abstract:

Several series of biaryloxatropenes with a double bond at the 2-3 carbon atoms of the 7-membered ring system were synthesized (20 examples) via palladium catalyzed cross coupling reactions in 72-93% yields. The bioactive 2-carbomethoxy-3-biaryl-8-oxabicyclo[3.2.1]octenes contained various heteroaryl subunits at the 3-position of tropane skeleton were subjected to samarium iodide reduction, which produced both of the 2β-carbomethoxy-3-biaryl-8-oxabicyclo[3.2.1]octane diastereomers and the 2α-carbomethoxy-3-biaryl-8-oxabicyclo[3.2.1]octane diastereomers (22 examples). Among the five series synthesized, the benzothiophene substituted compounds demonstrated outstanding profiles of inhibition of WIN 35,438 with 177 fold selectivity for DAT vs. SERT.