Eric D. Dowdy

A novel method for the mild and selective amidation of diesters and the amidation of monoesters

Abstract The selective monoamidation of diesters and amidation of esters mediated by Lewis acids are described. The selective amidations of dimethyl pyridine-2,5-dicarboxylate ( 1) and dimethyl 2,3-indole-dicarboxylate ( 4) with primary and secondary amines mediated by MgCl 2 or MgBr 2 under mild conditions gave the corresponding ester-amides in high yield.

Practical synthesis of the rebeccamycin aglycone and related analogs by oxidative cyclization of bisindolylmaleimides with a Wacker-type catalytic system

Abstract Using atmospheric O 2 as the stoichiometric oxidant, Pd 2+ /Cu 2+ -catalyzed oxidative cyclization of the corresponding bisindolylmaleimides provides the rebeccamycin aglycone and related indolo[2,3- a ]pyrrolo[3,4- c ]carbazoles in 58–88% yield. The method is operationally simple and utilizes readily prepared substrates, making the process amenable to scaleup.

Electronic effects in the acid-promoted deprotection of N-2,4-dimethoxybenzyl maleimides

Abstract Cleavage of several 2,4-dimethoxybenzylmaleimides could be performed employing TFA in anisole. Electronic effects exemplified by varying the substitution present on the maleimide resulted in a variation in the rate of the deprotection. In contrast, 2,4-dimethoxybenzylsuccinimides were inert to the conditions.