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Issue 13, 2011
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Stereoselective synthesis of complex polycyclic aziridines: use of the Brønsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally protected mitomycin C intermediate with maximal convergency

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Abstract

A concise synthesis of a highly functionalized intermediate lacking only C10 of the mitomycin backbone is described. The key to this development is the Brønsted acid-catalyzed aza-Darzens reaction used to forge the cis-aziridine. Additionally an oxidative ketalization fortuitously occurs during the quinoneenamine coupling step, leading to an orthogonally protected hydroquinone.

Graphical abstract: Stereoselective synthesis of complex polycyclic aziridines: use of the Brønsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally protected mitomycin C intermediate with maximal convergency

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Publication details

The article was received on 22 Dec 2010, accepted on 10 Feb 2011 and first published on 24 Feb 2011


Article type: Communication
DOI: 10.1039/C0CC05734G
Citation: Chem. Commun., 2011,47, 3975-3977
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    Stereoselective synthesis of complex polycyclic aziridines: use of the Brønsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally protected mitomycin C intermediate with maximal convergency

    J. M. Srinivasan, P. A. Mathew, A. L. Williams, J. C. Huffman and J. N. Johnston, Chem. Commun., 2011, 47, 3975
    DOI: 10.1039/C0CC05734G

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