Diastereoselective synthesis of beta-lactams using polyaromatic imines

ORGN 100

Bimal K. Banik, banik@panam.edu1, Indrani Banik2, and Frederick F. Becker2. (1) Department of Chemistry, The University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541, (2) Department of Molecular Pathology, The University of Texas M. D. Anderson Cancer Center, 1515 Holcombe Blvd., Houston, TX 77030

We have demonstrated various methods for the synthesis of b-lactams and several other biologically active compounds.  In continuation of our research in this area, we describe herein an account of our stereocontrolled synthesis of novel anticancer b-lactams starting from polyaromatic imines.  The preparation of b-lactams using the Staudinger reaction was discovered more than 90 years ago.  Surprisingly, there has not been a precedent recorded in the literature regarding the use of tetracyclic or pentacyclic aromatic systems in imine components.  Notably, the formation of trans-b-lactams as seen in the present investigation also has not been described in the literature.  These extensive results also indicate that it is the nature of the C4 group that controls the isomer distribution in this type of reaction.