Synthetic approaches to pallimamine and analogues using direct imine acylation

Thomas O. Ronson; Christiana Kitsiou; William P. Unsworth; Richard J K Taylor

doi:10.1016/j.tet.2016.05.009

Synthetic approaches to pallimamine and analogues using direct imine acylation

Thomas O. Ronson, Christiana Kitsiou, William P. Unsworth^*, Richard J K Taylor

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The use of Direct Imine Acylation (DIA) methodology for the total synthesis of pallimamine is described, with three different synthetic routes examined. The construction of three advanced δ-lactam precursors, all utilising DIA, is described, along with attempts to progress these compounds further, using three distinct desymmetrisation strategies, two involving alcohol-aryl coupling, and a third involving an unusual diastereoselective lactonisation.

Original language	English
Number of pages	8
Journal	Tetrahedron
Early online date	13 May 2016
DOIs	https://doi.org/10.1016/j.tet.2016.05.009
Publication status	E-pub ahead of print - 13 May 2016

Bibliographical note

Keywords

Berberine alkaloids
Imines
N-acyliminium ions
Nitrogen heterocycles
Pallimamine

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10.1016/j.tet.2016.05.009Licence: CC BY

1-s2.0-S0040402016303829-main
© 2016 The Authors.
Final published version, 931 KBLicence: CC BY-ND

Cite this

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abstract = "The use of Direct Imine Acylation (DIA) methodology for the total synthesis of pallimamine is described, with three different synthetic routes examined. The construction of three advanced δ-lactam precursors, all utilising DIA, is described, along with attempts to progress these compounds further, using three distinct desymmetrisation strategies, two involving alcohol-aryl coupling, and a third involving an unusual diastereoselective lactonisation.",

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AU - Ronson, Thomas O.

AU - Kitsiou, Christiana

AU - Unsworth, William P.

AU - Taylor, Richard J K

PY - 2016/5/13

Y1 - 2016/5/13

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KW - Berberine alkaloids

KW - Imines

KW - N-acyliminium ions

KW - Nitrogen heterocycles

KW - Pallimamine

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SN - 0040-4020

JO - Tetrahedron

JF - Tetrahedron

ER -

Synthetic approaches to pallimamine and analogues using direct imine acylation

Abstract

Bibliographical note

Keywords

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Raw data for the paper 'Synthetic approaches to pallimamine and analogues using direct imine acylation'

Cite this

Synthetic approaches to pallimamine and analogues using direct imine acylation

Abstract

Bibliographical note

Keywords

Access to Document

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Raw data for the paper 'Synthetic approaches to pallimamine and analogues using direct imine acylation'

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