Improved synthesis of n-methylcadaverine

Kayla N. Anderson; Shiva Moaven; Daniel K. Unruh; Anthony F. Cozzolino; John C. D’Auria

doi:10.3390/molecules23051216

Improved synthesis of n-methylcadaverine

Kayla N. Anderson, Shiva Moaven, Daniel K. Unruh, Anthony F. Cozzolino, John C. D’Auria

Chemistry and Biochemistry

Research output: Contribution to journal › Article

Abstract

Alkaloids compose a large class of natural products, and mono-methylated polyamines are a common intermediate in their biosynthesis. In order to evaluate the role of selectively methylated natural products, synthetic strategies are needed to prepare them. Here, N-methylcadaverine is prepared in 37.3% yield in three steps. The alternative literature two-step strategy resulted in reductive deamination to give N-methylpiperidine as determined by the single crystal structure. A straightforward strategy to obtain the mono-alkylated aliphatic diamine, cadaverine, which avoids potential side-reactions, is demonstrated.

Original language	English
Article number	1216
Journal	Molecules
Volume	23
Issue number	5
DOIs	https://doi.org/10.3390/molecules23051216
State	Published - 2018

Keywords

Alkaloid
Granatane
N-methylcadaverine
N-methylpiperidine. reductive deamination

Access to Document

10.3390/molecules23051216

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Anderson, K. N., Moaven, S., Unruh, D. K., Cozzolino, A. F., & D’Auria, J. C. (2018). Improved synthesis of n-methylcadaverine. Molecules, 23(5), [1216]. https://doi.org/10.3390/molecules23051216

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AU - D’Auria, John C.

PY - 2018

Y1 - 2018

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AB - Alkaloids compose a large class of natural products, and mono-methylated polyamines are a common intermediate in their biosynthesis. In order to evaluate the role of selectively methylated natural products, synthetic strategies are needed to prepare them. Here, N-methylcadaverine is prepared in 37.3% yield in three steps. The alternative literature two-step strategy resulted in reductive deamination to give N-methylpiperidine as determined by the single crystal structure. A straightforward strategy to obtain the mono-alkylated aliphatic diamine, cadaverine, which avoids potential side-reactions, is demonstrated.

KW - Alkaloid

KW - Granatane

KW - N-methylcadaverine

KW - N-methylpiperidine. reductive deamination

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