Daniel E. Petrillo

Improved syntheses of α-BOC-aminoketones from α-BOC-amino-Weinreb amides using a pre-deprotonation protocol

Abstract A general procedure was developed to prepare α-BOC-aminoketones in good yields from α-BOC-amino Weinreb amides containing an exchangeable amino proton. By first deprotonating this amino group using 1 equiv. of a simple alkyl Grignard base, only a stoichiometric amount, rather than a large excess, of the nucleophile was needed to prepare the ketone. This procedure is therefore more economical to run and the purification is easier.

Practical synthesis of a potent indolocarbazole-based, DNA topoisomerase inhibitor

Abstract DNA topoisomerase I inhibitors are currently under investigation as cancer chemotherapy agents of which indolocarbazole glycoside ( 1 ) has been identified as a promising candidate. A practical, scalable synthesis of 1 that limits the isolation of cytotoxic compounds to only that of the final product is described. The convergent process features a novel phase transfer-promoted glycosylation of aglycone core ( 4 ); subsequent hydrolysis provides anhydride ( 8 ). The hydrazine fragment ( 3 ), which is coupled with 8 , is synthesized via a modification of existing procedures. The coupled product ( 2 ) is subsequently hydrogenated to provide 1 in excellent purity via direct crystallization (>99.3 A%).