Synthesis of 6,7-benzene-fused tropane derivatives from isoindoline-aminal hybrid compound
2022
Tsujihara, Tetsuya | Sasaki, Ryota | Fukkoshi, Mizuki | Hatakeyama, Sae | Takehara, Tsunayoshi | Suzuki, Takeyuki | Kawano, Tomikazu
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.
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