Studies on the Total Synthesis of CC-1065: Preparation of a Synthetic, Simplified 3-Carbamoyl-1,2-dihydro-3H-pyrroloindole Dimer/Trimer/Tetramer (CDPI Dimer/Trimer/Tetramer) and Development of Methodolodgy for PDE-I Dimer Methyl Ester Formation

Article abstract of DOI:10.1021/jo00384a026

Two synthetic preparations of 3-carbamaoyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole-7-carboxylic acid (2b, CDPI) and the investigation and development of methodology for the preparation of 3-carbamoyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole dimer 3 (CDPI dimer) constituting the simplified and stable PDE-I dimer skeleton possessing the B-DNA minor groove complementary shape of the natural product CC-1065 are detailed.The extension of this methodology to the preparation of 3-carbamoyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole trimer 4 and tetramer 5 (CDPI trimer and tetramer) are described and constitute synthetic, potentially selective, high affinity, noncovalent B-DNA minor groove binding agents.