Extending Pummerer reaction chemistry: (+/-)-dibromoagelaspongin synthesis and related studies.
The sponge-derived alkaloid dibromoagelaspongin was prepared from a dihydrooroidin derivative by exploiting the Pummerer reaction twice in succession. Oxidative cyclization of the substrate's pyrrole-2-carboxamide function into the imidazole moiety was achieved in a regiospecific manner to establish both C-N bonds to C(6) of the target.
Feldman
Ken S
KS
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu
Fodor
Matthew D
MD