Bidirectional synthesis of montamine analogs

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 acetat...

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Bibliographic Details
Published in:Tetrahedron letters 2013-10, Vol.54 (40), p.5489-5491
Main Authors: Freitas, Melanie B., Simollardes, Kelly A., Rufo, Caroline M., McLellan, Chantel N., Dugas, Gabrielle J., Lupien, Leslie E., Davie, Elizabeth A. Colby
Format: Article
Language:English
Subjects:
Alkaloids
Alkylation
Analogs
Aryl ether demethylation
Bidirectional
Bidirectional synthesis
Chlorides
Ferulic acid
Fischer indole synthesis
Hydrazides
Montamine
Synthesis (chemistry)
Tetrahedrons
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.07.134