Carboxylates polycyclic pyrrole

In 2005, Yamamoto et al. reported the synthesis of polycyclic pyrrole-2-carboxylates 76 via a CuBr -catalyzed three-component coupling of A-benzylallylamine, ethyl gly-oxalate, and terminal alkynes, and subsequent ttansforma-tion of the glycine-tethered 1,6-enynes 75 thus obtained through a cycloisomerization/Diels-Alder cycloaddition/ dehydrogenation sequence under iridium-catalyzed conditions (Scheme 3.43) [108]. 

SCHEME 343 Synthesis of polycyclic pyrrole-2-carboxylates via CuAAC/cycloisomerization/Diels-Alder cycloaddition/dehydrogena-tion sequence. 

Y. Yamamoto, H. Hayashi, T. Saigoku, H. Nishiyama, J. Am. Chem. Soc. 2005, 127, 10804-10805. Domino coupling relay approach to polycyclic pyrrole-2-carboxylates. 

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