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

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Authors
Hall, Edward A.
Advisor
Sammelson, Robert E.
Issue Date
2009
Keyword
Degree
Thesis (B.?.)
Department
Honors College
Other Identifiers
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.