Total synthesis of Lavendamycin derivatives : an honors thesis (HONRS 499)

Abstract

Derivatives of Lavendamycin, an antitumor antibiotic natural product, were synthesized via short and efficient methods. Pictet-Spengler condensation of 7Nbutryamido-2-formylquinoline-5,8-dione (11) with neutralized tryptophan amide afforded 7N-butryamidodemethyllavendamycin (13). 7N-Butyramdio-2formylquinoline-5,8-dione (11) was prepared by the oxidation of 7N-butryamdio2-methylquinoline-5,8-dione (8). Novel 7 -methoxy-2-formylquinoline-5,8-dione (19) was prepared via oxidative deprotection of2-( dimethoxymethyl)-7methoxyquinoline-5,8-dione (18). A newly synthesized lavendamycin derivative is reported in compound 20.