| Compound 593A and naphthyridinomycin are both naturally occurring antibiotics. They both have novel structural features which present challenges to the synthetic chemist.;The first and, to date, only total synthesis of d,1-antibiotic 593A is described herein. A novel feature of this synthesis is the dimerization of an activated cis (alpha)-amino-(beta)-lactam to not only form the central piperazinedione but also to control four of the six asymmetric centers.;Approaches toward the total synthesis of naphthyridinomycin, a novel quinone alkaloid, are also described. Interesting features include a cation-olefin cyclization to form a functionalized pyrrolidine and a proposed intramolecular attack of nitrogen on a quinone methide. |
