NATURAL PRODUCT SYNTHESIS: TOTAL SYNTHESIS OF D,1-ANTIBIOTIC 593A. SYNTHETIC APPROACHES TOWARD NAPHTHYRIDINOMYCIN
FRANK, RICHARD KEITH
Doctor of Philosophy
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.