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

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 quinone-enamine coupling step, leading to an orthogonally protected hydroquinone.

SUBMITTER: Srinivasan JM

PROVIDER: S-EPMC3334326 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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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.

Srinivasan Jayasree M JM Mathew Priya A PA Williams Amie L AL Huffman John C JC Johnston Jeffrey N JN

Chemical communications (Cambridge, England) 20110224 13

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 quinone-enamine coupling step, leading to an orthogonally protected hydroquinone. ...[more]

PMID: 21347494

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