Substrate scope in the direct imine acylation of ortho-substituted benzoic acid derivatives: the total synthesis (±)-cavidine

Christiana Kitsiou; William P. Unsworth; Graeme Coulthard; Richard J K Taylor

doi:10.1016/j.tet.2014.04.066

Substrate scope in the direct imine acylation of ortho-substituted benzoic acid derivatives: the total synthesis (±)-cavidine

Christiana Kitsiou, William P. Unsworth, Graeme Coulthard, Richard J K Taylor^*

^*Corresponding author for this work

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

Abstract

The direct imine acylation (DIA) and subsequent cyclisation of a range of imines with ortho-substituted benzoic acid derivatives is described. Variation in the coupling reagents, imine and benzoic acid were all examined. The DIA procedure was also applied in the total synthesis of (±)-cavidine.

Original language	English
Pages (from-to)	7172-7180
Number of pages	9
Journal	Tetrahedron
Volume	70
Issue number	40
Early online date	1 May 2014
DOIs	https://doi.org/10.1016/j.tet.2014.04.066
Publication status	Published - 7 Oct 2014

Keywords

Cavidine
Evodiamine
Molecular diversity
N-Acyliminium ions
Nitrogen heterocycles

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10.1016/j.tet.2014.04.066

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abstract = "The direct imine acylation (DIA) and subsequent cyclisation of a range of imines with ortho-substituted benzoic acid derivatives is described. Variation in the coupling reagents, imine and benzoic acid were all examined. The DIA procedure was also applied in the total synthesis of (±)-cavidine.",

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AU - Coulthard, Graeme

AU - Taylor, Richard J K

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AB - The direct imine acylation (DIA) and subsequent cyclisation of a range of imines with ortho-substituted benzoic acid derivatives is described. Variation in the coupling reagents, imine and benzoic acid were all examined. The DIA procedure was also applied in the total synthesis of (±)-cavidine.

KW - Cavidine

KW - Evodiamine

KW - Molecular diversity

KW - N-Acyliminium ions

KW - Nitrogen heterocycles

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M3 - Article

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ER -

Substrate scope in the direct imine acylation of ortho-substituted benzoic acid derivatives: the total synthesis (±)-cavidine

Abstract

Keywords

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