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Issue 8, 2009
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Cascade condensation, cyclization, intermolecular dipolar cycloaddition by multi-component coupling and application to a synthesis of (±)-crispine A

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Abstract

A general approach for the synthesis of various nitrogen-containing heterocyclic compounds is described using an intermolecular dipolar cycloaddition reaction of azomethine ylides and nitrones. Stabilized and non-stabilized azomethine ylide dipoles or the related nitrones were generated by condensation of 4-, 5- or 6-halo-aldehydes with a readily available amino-acid, amino-ester or hydroxylamine to give an imine followed by cyclization and either decarboxylation or loss of a proton. After intermolecular cycloaddition with an activated dipolarophile, bicyclic or polycyclic (if the ylide dipole and/or dipolarophile contain a ring) amines were produced. A short synthesis of the alkaloid (±)-crispine A was achieved based on this tandem/domino 3-component coupling chemistry.

Graphical abstract: Cascade condensation, cyclization, intermolecular dipolar cycloaddition by multi-component coupling and application to a synthesis of (±)-crispine A

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Publication details

The article was received on 18 Dec 2008, accepted on 02 Feb 2009 and first published on 06 Mar 2009


Article type: Paper
DOI: 10.1039/B822743H
Citation: Org. Biomol. Chem., 2009,7, 1674-1679
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    Cascade condensation, cyclization, intermolecular dipolar cycloaddition by multi-component coupling and application to a synthesis of (±)-crispine A

    I. Coldham, S. Jana, L. Watson and N. G. Martin, Org. Biomol. Chem., 2009, 7, 1674
    DOI: 10.1039/B822743H

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