Herein, the synthesis of 6,7-benzene-fused tropane derivatives from isoindoline-aminal hybrid compound has been reported. In the present synthetic study, ring-closing metathesis (RCM) was employed to construct the 6,7-benzene-fused tropene skeleton. To obtain the desired cis-1-allyl-3-stylylisoindoline precursor for the RCM reaction, the diastereoselective aza-Hosomi-Sakurai allylation and functional group transformations of isoindoline-aminal hybrid compound were performed. Using the synthesized 6,7-benzene-fused tropene derivative as a versatile precursor, synthesis of several 6,7-benzene-fused tropane derivatives was demonstrated by the transformations of the internal alkene moiety.(c) 2022 Elsevier Ltd. All rights reserved.
Key words
Direct amidation/Aza-Michael reaction/Aza-Hosomi-Sakurai allylation/Tropane derivatives/CYCLOADDITION/CONSTRUCTION/COMBINATION/PIPERIDINES/ACCESS
NSTL
Elsevier