98468-21-4Relevant academic research and scientific papers
Bidirectional synthesis of montamine analogs
Freitas, Melanie B.,Simollardes, Kelly A.,Rufo, Caroline M.,McLellan, Chantel N.,Dugas, Gabrielle J.,Lupien, Leslie E.,Davie, Elizabeth A. Colby
supporting information, p. 5489 - 5491 (2013/09/23)
Reported herein is a bidirectional synthesis of symmetric N,N′-diacyl hydrazide compounds closely resembling the alkaloid natural product montamine. In the process, di-tert-butyl hydrazine-1,2-dicarboxylate was smoothly dialkylated with alkyl halides, then Boc deprotected and acylated with an acetate-protected acid chloride derived from ferulic acid. After acetate removal, simple montamine analogs were obtained in excellent overall yields. Fischer indole synthesis with 4-methoxyphenylhydrazine hydrochloride and dihydrofuran provided 5-methoxytryptophol, which was then elaborated to the 1,2-bis(5-methoxyindol-3-yl)hydrazide structure bearing the substitution pattern found in montamine.
